GB1299100A - Substituted pyridines and dihydropyridines - Google Patents

Substituted pyridines and dihydropyridines

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Publication number
GB1299100A
GB1299100A GB53254/70A GB5325470A GB1299100A GB 1299100 A GB1299100 A GB 1299100A GB 53254/70 A GB53254/70 A GB 53254/70A GB 5325470 A GB5325470 A GB 5325470A GB 1299100 A GB1299100 A GB 1299100A
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United Kingdom
Prior art keywords
prepared
pyridone
nitro
methyl
ethyl
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Expired
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GB53254/70A
Inventor
Bruce Edward Witzel
Tsung-Ying Shen
Patricia M Graham
Robert L Clark
Arsenio A Pessolano
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Merck and Co Inc
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Merck and Co Inc
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Publication of GB1299100A publication Critical patent/GB1299100A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

1299100 Substituted pyridines and dihydropyridines MERCK & CO Inc 9 Nov 1970 [12 Nov 1969] 53254/70 Heading C2C Novel compounds I and II in which L is H, alkyl, alkenyl, alkynyl, aralkyl, substituted benzyl, aryl, substituted phenyl, hydroxyalkyl, amino, dialkylamino, dialkylaminoalkyl, carboxyalkyl, alkylaminoalkyl, haloalkyl, alkylamino, alkanoylaminoalkyl, hydroxy, N - alkanoylalkylaminoalkyl, aralkenyl, alkoxy or heterocyclyl; each R<SP>0</SP> is H, acyl or alkoxycarbonyl; X is O or S; Z is H, alkyl or aryl; and each of R 1 , R 2 and R 3 is H, haloalkyl, alkylthio, alkylsulphinyl, alkylsulphonyl, OH, sulphonamido, sulpho, carboxyalkyl, alkoxy, alkenyloxy, alkoxycarbonyl, alkoxyalkyl, arylthio, aralkylthio, acylamino, hydroxyalkyl, acyl, alkenyl, alkynyl, alkyl, cycloalkyl, NO 2 , carbamoyl, N-alkyl or N,N- dialkyl - carbamoyl or N - arylcarbamoyl with the provisos that if one of R 1 -R 3 is alkyl or NO 2 the other two must be H; that if one of R 1 -R 3 is acyl, the other two must be other than alkyl and that at least one of R 1 -R 3 must be other than H; are prepared (1) by reduction of compounds III (2) by reaction of compounds IV with P 2 S 5 to give I where L is H, R‹ is H and X is S; (3) by introducing a radical L<SP>1</SP> at the 1- position of a compound III by normal methods followed by reduction of the NO 2 group; (4) by reduction of compounds V (5) by acylation of the amino group in a compound VI (6) by cleaving the ether or thioether group in a compound II to give a compound I in which L is H. 2 - Amino - 4 - ethyl - pyridine (A) is prepared by reacting 4-ethylpyridine with sodamide. 2 - Amino - 3 - nitro - 4 - ethyl - pyridine (B) is prepared by nitration of (A). Similarly to B are prepared 2 - amino - 3 - nitro - 5 - methyl-; 2 - amino - 3 - nitro - 4,5,6 - trimethyl-; 2- amino - 3 - nitro - 4 - ethyl - 5 - fluoro and 2- amino - 3 - nitro - 5 - ethyl - 6 - trifluoromethylpyridine. 4 - Ethyl - 3 - nitro - 2[1H] - pyridone is prepared by diazotization of 2-amino-4-ethyl- 3 - nitropyridine. 4 - t - Butyl - pyridine - N- oxide is prepared by reacting 4 - t - butyl. pyridine with H 2 O 2 . 4-t-Butyl-2[1H]-pyridone is prepared by reacting the previously named intermediate with acetic anhydride or by reaction with SO 2 Cl 2 and hydrolysis of the 2- chloro-derivative formed. 4-t-Butyl-5-nitro- 2[1H] - pyridone - 5 - methyl - 3 - nitro - 2[1H]- pyridone and 4 - ethyl - 5 - fluoro - 3 - nitro- 2[1H]-pyridone are prepared by nitration of the corresponding non-nitrated compounds. 5- Bromo - 4 - ethyl - 3 - nitro - 2[1H] - pyridone is prepared by bromination of the non-brominated compound, e.g. with Br 2 or N-bromosuccinimide. 5 - Methylthio - 4 - ethyl - 3 - nitro- 2[1H]-pyridone is prepared by reacting the corresponding 5-bromo-derivative with copper methylthiolate. 4 - t - Butyl - 5 - cyano - 3 - nitro- 2[1H]-pyridone is prepared by reaction of the 5-bromo-derivative with cuprous cyanide. 5- Chloro - 3 - nitro - 4 - methyl - 2[1H] - pyridone is prepared by reaction of the non-chlorinated compound with N-chlorosuccinimide under N 2 - 2 - Chloro - 6 - methyl - nicotinoyl chloride is prepared by reaction of 3-carboxy-6-methyl. 2[1H]-pyridone with PCl 5 and POCl 3 . 2-Chloro- 6 - methyl - 3 - trifluoromethyl - pyridine is prepared by reacting the previously mentioned acid chloride with HF. 6-Methyl - 3 - trifluoromethyl-2[1H]-pyridone is prepared from the last named intermediate by reaction with silver acetate and acetic acid followed by hydrolysis. 3 - Acetyl - 6 - methyl - 2[1H] - pyridone, is prepared by reaction of 3-cyano-6-methyl- 2[1H]-pyridone with methyl magnesium iodide. 3 Acetyl - 5 - nitro - 6 - methyl - 2[1H] - pyridone is prepared by nitration of the non-nitrated com - pound. 5 - Methylsulphinyl and 5 - methylsulphonyl - 4 - ethyl - 3 - nitro - 2[1H] - pyridone is prepared by oxidation of the 5-methylthio compound. 3 - Amino - 6 - ethyl - 5 - nitro - 2[1H]-pyridone is prepared by nitration of the corresponding non-nitrated compound. 5- Carbamoyl - 4 - methyl - 3 - nitro - 2[1H]- pyridone is prepared by partial hydrolysis of the 'relevant 5 - cyano compound. 4 - Carboxymethyl - 3 - nitro 2[1H] - pyridone is prepared by reaction of the corresponding 4-methyl compound with butyl lithium and solid CO 2 . 4 - t - Butyl - 1 - methyl - 3 - nitro - 2[1H]- pyridone is prepared by N-methylation. 4-t- Butyl 1 - phenyl - 3 - nitro - 2[1H] - pyridone is prepared by N-phenylation. 5-Ethyl-3-nitro- 1 - tetrahydropyran - 2 - yl - 2[1H] - pyridone is prepared by reaction of the N-unsubstituted compound with dihydropyran- 3-Amino-6- methyl 2[1H] - pyridone - 5 - sulphonic acid is prepared by reacting chlorosulphonic acid with 3 - nitro - 6 - methyl - 2[1H] - pyridone. 3- Nitro - 6 - methyl - 2[1H] - pyridone - 5 - sulphonamide is prepared by reaction of the above sulphonic acid with diazomethane followed by concentrated NH 4 OH. 6-Benzylthio-3-nitro- 2[1H]-pyridone is prepared by reaction of benzene thiol with the appropriate 6-chloro-compound. 2 - Chloro - 3 - nitro - 5 - ethyl - pyridone is prepared by reacting 3-nitro-5-ethyl-2[lH]- pyridone with PCl 5 and POCl 3 . 3-Nitro-5-ethyl- 2-methoxypyridine is prepared by reaction of the 2-chloro compound with CH 3 ONa. 3-Fluoro- 4 - methyl - pyridine - N - oxide is prepared by reaction of 3 - fluoro - 4 - methyl - pyridine with H 2 O 2 . 2 - Chloro - 3 - fluoro - 4 - methyl - pyridine is prepared by reaction of the above N- oxide with SO 2 Cl 2 . 3-Fluoro-4-methyl-2[1H]- pyridone is prepared by hydrolysis of the 2- chloro - derivative. 1 - Amino - 4 - t - butyl- 3 - nitro - 2[1H] - pyridone is prepared by reaction of sodium salt of 4-(-butyl-3-nitro- 2[1H]-pyridone and chloramine. Pharmaceutical compositions useful as antiinflammatory agents for enteral and parenteral administration comprise a compound I together with a suitable excipient.
GB53254/70A 1969-11-12 1970-11-09 Substituted pyridines and dihydropyridines Expired GB1299100A (en)

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US87605969A 1969-11-12 1969-11-12

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US (1) US3654291A (en)
JP (1) JPS4815950B1 (en)
BE (1) BE758759A (en)
CA (1) CA968803A (en)
CH (1) CH549569A (en)
DE (1) DE2055513A1 (en)
ES (1) ES385397A1 (en)
FR (1) FR2073341B1 (en)
GB (1) GB1299100A (en)
IL (1) IL35568A (en)
NL (1) NL7015826A (en)
NO (1) NO133669C (en)
SE (1) SE386439B (en)
ZA (1) ZA707636B (en)

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US3721676A (en) * 1969-11-12 1973-03-20 Merck & Co Inc Certain 3-amino-2(1h)pyridones
GB1419994A (en) * 1973-05-03 1976-01-07 Smith Kline French Lab Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them
US4035374A (en) * 1973-05-03 1977-07-12 Smith Kline & French Laboratories Limited Imidazolyl alkylaminopyridone and pyridinethione compounds
US4578459A (en) * 1973-05-03 1986-03-25 Smithkline & French Laboratories Limited Heterocyclic alkylaminoheterocycles
US4260744A (en) * 1973-05-03 1981-04-07 Smith Kline & French Laboratories Limited Pharmacologically active compounds
US4467087A (en) * 1973-05-03 1984-08-21 Smith Kline & French Laboratories Limited 1,2,4-Triazines
DE3106460A1 (en) * 1980-03-03 1982-01-28 Sandoz-Patent-GmbH, 7850 Lörrach 2 (1H) -PYRIDINONE DERIVATIVES, THEIR PRODUCTION AND THE PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
US4371537A (en) * 1981-08-13 1983-02-01 The Dow Chemical Company Sulfur-substituted phenoxypyridines having antiviral activity
US4412077A (en) * 1982-03-15 1983-10-25 Sterling Drug Inc. Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone
US4524149A (en) * 1982-03-15 1985-06-18 Sterling Drug Inc. 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use
US4451469A (en) * 1982-12-16 1984-05-29 Sterling Drug Inc. Selected 6-alkyl-and 4,6-dialkyl-2(1H)-pyridinones as cardiotonics
US4681873A (en) * 1985-07-29 1987-07-21 Warner-Lambert Company 4-amino-3-halo-2-pyridinone nucleoside and nucleotide compounds
US5164506A (en) * 1988-12-14 1992-11-17 Bayer Aktiengesellschaft Substituted 2-pyridones and pyrid-2-thiones compounds
US5032602A (en) * 1988-12-14 1991-07-16 Bayer Aktiengesellschaft Inhibiting HMG-CoA reductase with novel substituted 2-pyridones and pyrid-2-thiones
US5308854A (en) * 1990-06-18 1994-05-03 Merck & Co., Inc. Inhibitors of HIV reverse transcriptase
GB9016578D0 (en) * 1990-07-27 1990-09-12 Ici Plc Fungicides
AU2007202607B2 (en) * 2002-02-14 2008-12-18 Pharmacia Corporation Substituted Pyridinones as Modulators of p38 MAP Kinase
PL218749B1 (en) * 2002-02-14 2015-01-30 Pharmacia Corp Substituted pyridinones as modulators of p38 map kinase
KR100901931B1 (en) 2002-02-14 2009-06-10 파마시아 코포레이션 Substituted Pyridinones as Modulators of P38 MAP Kinase
CL2004002050A1 (en) * 2003-08-13 2005-06-03 Pharmacia Corp Sa Organizada B COMPOUNDS DERIVED FROM REPLACED PIRIDINONES; ITS USE IN THE TREATMENT OF AFFECTIONS CAUSED OR EXACTED BY ACTIVITY P38 MAP KINASA AND / OR NON-REGULATED TNF, SUCH AS INFLAMMATIONS, TUMORS, AIDS AND OTHERS.
US10696635B2 (en) * 2016-04-18 2020-06-30 The Scripps Research Institute Versatile ligand for palladium-catalyzed meta-C—H functionalizations of aromatic substrates

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DE596728C (en) * 1932-10-26 1934-05-09 Chem Fab Von Heyden Akt Ges Process for the preparation of 2-oxy-5-aminopyridine or its core substitution products
DE626687C (en) * 1934-07-05 1936-09-01 Chem Fab Von Heyden Akt Ges Process for the preparation of alkoxyaminopyridines
NL6816241A (en) * 1967-12-01 1969-06-03

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NL7015826A (en) 1971-05-14
US3654291A (en) 1972-04-04
FR2073341A1 (en) 1971-10-01
NO133669B (en) 1976-03-01
IL35568A0 (en) 1971-01-28
CA968803A (en) 1975-06-03
SE386439B (en) 1976-08-09
CH549569A (en) 1974-05-31
ES385397A1 (en) 1973-11-01
ZA707636B (en) 1972-06-28
DE2055513A1 (en) 1971-05-19
FR2073341B1 (en) 1973-08-10
NO133669C (en) 1976-06-09
IL35568A (en) 1974-09-10
JPS4815950B1 (en) 1973-05-18
BE758759A (en) 1971-05-10

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