Sterling Drug Inc.

Sanofi

Sterling Winthrop Inc.

Philip M Carabateas

Guy D Diana

Malcolm R Bell

Virendra Kumar

John P Mallamo

Thomas E D'Ambra

Susan J Ward

Michael A Eissenstat

Gordon L Williams

Edward R Bacon

George Y Lesher

Baldev Singh

Ruth P Brundage

Edward Richard Bacon

2-R.sub.2 --R.sub.4 -substituted-3-R.sub.3 --CO-1-�(C-attached-N-heteryl)-(Alk) .sub.n !-1H-indoles useful as analgesic, anti-rheumatic, anti-inflammatory or anti-glaucoma agents.

3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles

2-R.sub.2 -R.sub.4 -substitutea-3-R.sub.3 -CO-1-[(C-attached-N-heteryl)(Alk).sub.n ]-1H-indoles useful as analgesic, anti-rheumatic, anti-inflammatory or anti-glaucoma agents.

2-R.sub.2 -R.sub.4 -substituted-3-R.sub.3 -CO-1-[(C-attached-N-herteryl)-(Alk).sub.n ]-1H-indoles useful as analgesic, anti-rheumatic, anti-inflammatory or anti-glaucoma agents.

Compounds of the formula ##STR1## wherein the substituents are as defined herein are useful as antiviral agents, in particular against picornaviruses.

Dihydro-oxazolyl substituted-phenyl-aliphatic lower alkyl and their use

Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;

Heterocyclic substituted-phenoxyalkylisoxazoles as antiviral useful

3,4-Dihydro-3-R.sub.1 -4-R.sub.2 -5-Q-6-R-2(1H)-pyridinones (I), where R.sub.1 and R.sub.2 are each hydrogen or methyl, R is lower-alkyl, and Q is 4(or 3)-hydroxyphenyl, 4(or 3)-methoxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof, and their preparation are shown. Also shown is the cardiotonic use of I where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents.

2-Pyridinones and their use as cardiotonic agents

4-(Arylaliphatic)isoxazoles, having antiviral activity, are prepared by reacting with hydroxylamine a diketone of the formula Ar-Y-CH(CO-R).sub.2, wherein Ar is substituted phenyl, Y is (CH.sub.2).sub.n or O(CH.sub.2).sub.n, and R is lower-alkyl.

4-(Arylaliphatic)isoxazoles

4-(Aryloxyalkyl)pyrazoles of the formula ##STR1## useful as antiviral agents, are prepared by reacting the corresponding diketones of the formula Ar--O--Alk--CH(COR')COR' with hydrazine or a substituted hydrazine H.sub.2 NNHR. Mono- or bis-pyrazoles are similarly obtained from bis-diketones of the formula ##STR2##

2-Benzoyl-8-(2-chloro-4-methoxyphenoxy)-1-phenyl-1-octanone

4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]

4-(Aryloxyalkyl)pyrazoles of the formula ##STR1## useful as antiviral agents, are prepared by reacting the corresponding diketones of the formula Ar-O-Alk-CH(COR')COR' with hydrazine or a substituted hydrazine H.sub.2 NNHR. Mono- or bis-pyrazoles are similarly obtained from bis-diketones of the formula ##STR2##

4-[6-(

Antiviral arylenedioxyalkyl substituted pyrazoles

Antiviral aryloxyalkylpyrazoles

Phenylenedioxy-bis-dikeones having the formula ##STR1## useful as antiviral agents, are prepared by etherification of dihydric phenols and alkylation of beta-dikeones.

Arylenedioxy-bis-diketones

4-(3-Nitrophenyl)pyridine, an intermediate useful in the preparation of 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylates, which are useful as antibacterial agents, is prepared by reacting 3-nitrobenzaldehyde with two molar equivalents of di-(lower-alkyl) oxalacetate (II) in the presence of a catalytic condensing agent, preferably piperidine and/or its acetate, to produce tetra-(lower-alkyl) 3-(3-nitrophenyl)-1,5-pentanedione-1,2,4,5-tetracarboxylate (III), reacting III with ammonia to produce tetra-(lower-alkyl) 1,4-dihydro-4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (IV), oxidizing IV to produce tetra-(lower-alkyl) 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (V), hydrolyzing V to produce 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylic acid (VI) and decarboxylating VI to produce 4-(3-nitrophenyl)pyridine (VI). Intermediates III, IV, V and VI are novel.

Tetra-(low

4-(3-Nitrophenylpyridine and intermediate useful in the preparation of 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylates, which are useful as antibacterial agents, is prepared by reacting 3-nitrobenzaldehyde with two molar equivalents of di-(lower-alkyl) oxalacetate (II) in the presence of a catalytic condensing agent, preferably piperidine and/or its acetate, to produce tetra-(lower-alkyl) 3-(3-nitrophenyl)-1,5-pentanedione-1,2,4,5-tetracarboxylate (III), reacting III with ammonia to produce tetra-(lower-alkyl) 1,4-dihydro-4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (IV), oxidizing IV to produce tetra-(lower-alkyl) 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (V), hydrolyzing V to produce 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylic acid (VI) and decarboxylating VI to produce 4-(3-nitrophenyl)pyridine (VI). Intermediates III, IV, V and VI are novel.

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Schodack, NY, United States of America

Philip M Carabateas