WO1981002575A1 - Derives de (1 h) -pyridinone, leur preparation et les compositions pharmaceutiques les contenant - Google Patents

Derives de (1 h) -pyridinone, leur preparation et les compositions pharmaceutiques les contenant Download PDF

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Publication number
WO1981002575A1
WO1981002575A1 PCT/CH1981/000023 CH8100023W WO8102575A1 WO 1981002575 A1 WO1981002575 A1 WO 1981002575A1 CH 8100023 W CH8100023 W CH 8100023W WO 8102575 A1 WO8102575 A1 WO 8102575A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
formula
carbon atoms
phenyl
alkyl
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.)
Ceased
Application number
PCT/CH1981/000023
Other languages
German (de)
English (en)
French (fr)
Inventor
G Bormann
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of WO1981002575A1 publication Critical patent/WO1981002575A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07D213/78—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

Definitions

  • R a 1 and R a 2 independently of one another i) hydrogen or alkyl with 1 to 4 carbon atoms, ii) phenyl, phenyl monosubstituted by di alkylamino with each independently 1 to 4 carbon atoms in each alkyl part, or phenyl mono- or identically or differently disubstituted by alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogen with an atomic number from 9 to 35 or iii) pyrrolyl, furanyl, thienyl, thiazolyl,
  • R a 1 preferably represents alkyl or the meaning given above ii) or iii).
  • R a 1 stands in particular for the above meaning ii).
  • R a 2 preferably stands for the above meaning i), in particular for methyl.
  • the meaning i) is preferably alkyl.
  • the meaning ii) is preferably unsubstituted or monosubstituted phenyl. If it is monosubstituted phenyl, the substituents are preferably in the m- or p-, in particular in the p-position. If it is disubstituted phenyl, the substituents are preferably in the m and p positions.
  • the substituents are preferably identical.
  • R a 1 and R a 2 has the meaning given above i).
  • R a 1 and R a 2 are not pyridinyl. They do not have the meaning iii) in a subgroup.
  • R a 1 a does not represent pyridinyl. In a subgroup, R a 1 a has the meaning given above ii).
  • Another group of compounds of the formula Ia consists of the compounds of the formula Ipa,
  • R p 1 a is hydrogen or alkyl having 1 to 4 carbon atoms and
  • R p 2 a has the meaning given above for R p 1 a .
  • Another group of compounds of the formula Ia consists of the compounds of the formula Ipc,
  • the amination process is carried out using conditions known for the preparation of analog 3-amino-2- (1H) -pyridinone compounds leads.
  • the group R x used is a conventional radical suitable for conversion into a primary amino group, such as nitro or, in particular, carbamoyl. If R x is carbamoyl, the procedure is, for example, under the conditions of Eofmann degradation. It is preferred to work in a strongly alkaline medium, for example in the presence of an alkali metal hydroxide and bromine. Water is preferably used as the solvent.
  • the temperature is about 50 ° to about 100 ° C, preferably about 100 ° C.
  • the compounds of the formula I can be isolated and purified in a known manner from the reaction mixture.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/CH1981/000023 1980-03-03 1981-02-27 Derives de (1 h) -pyridinone, leur preparation et les compositions pharmaceutiques les contenant Ceased WO1981002575A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH166880 1980-03-03
CH1668/80 1980-03-03
CH166980 1980-03-03
CH571780 1980-07-25
CH794780 1980-10-24

Publications (1)

Publication Number Publication Date
WO1981002575A1 true WO1981002575A1 (fr) 1981-09-17

Family

ID=27428258

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1981/000023 Ceased WO1981002575A1 (fr) 1980-03-03 1981-02-27 Derives de (1 h) -pyridinone, leur preparation et les compositions pharmaceutiques les contenant

Country Status (16)

Country Link
CA (1) CA1183533A (enExample)
CH (1) CH652395A5 (enExample)
DE (1) DE3106460A1 (enExample)
DK (1) DK94481A (enExample)
ES (1) ES499971A0 (enExample)
FI (1) FI810558L (enExample)
FR (1) FR2477148A1 (enExample)
GB (1) GB2070606B (enExample)
IL (1) IL62246A (enExample)
IT (1) IT1142458B (enExample)
NL (1) NL8100964A (enExample)
NZ (1) NZ196385A (enExample)
PT (1) PT72596B (enExample)
SE (1) SE8101336L (enExample)
WO (1) WO1981002575A1 (enExample)
YU (1) YU51581A (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666913A (en) * 1985-11-22 1987-05-19 William H. Rorer, Inc. Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses
US4785005A (en) * 1986-06-25 1988-11-15 Rorer Pharmaceutical Corporation 6-(6-alkylpyridone)-carbostyril compounds and their cardiotonic uses
EP0347027A3 (en) * 1988-04-21 1990-05-23 Smith Kline & French Laboratories Limited Phenylpyridone derivatives,processes for their preparation and pharmaceutical compositions containing them.
EP0428268A3 (en) * 1989-10-13 1991-11-27 Smith Kline & French Laboratories Limited Pharmaceutical phenylpyridone derivatives

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL65278A0 (en) * 1981-03-30 1982-05-31 Sterling Drug Inc 3-amino-5-(substituted)-2(1h)-pyridinones and corresponding 3-cyano compounds,their preparation and pharmaceutical compositions containing them
US4515797A (en) * 1981-09-08 1985-05-07 Sterling Drug Inc. 3-Amino-5-(hydroxy- and/or aminophenyl)-6-(lower-alkyl)-2(1H)-pyridinones and cardiotonic use thereof
US4465686A (en) * 1981-09-08 1984-08-14 Sterling Drug Inc. 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation
US4432979A (en) * 1981-10-26 1984-02-21 William H. Rorer, Inc. Pyridone compounds
US4539321A (en) * 1981-10-26 1985-09-03 William H. Rorer, Inc. 5-Diaza-aryl-3-substituted pyridone compounds
US4514400A (en) * 1981-10-26 1985-04-30 William H. Rorer, Inc. Cardiotonic 5-heteroaryl-pyridone
US4593028A (en) * 1981-10-26 1986-06-03 William H. Rorer, Inc. 5-hetero aryl-substituted-2-pyridones useful as cardiotonic agents for treatment of congestive heart failure
FR2527206B1 (fr) * 1982-05-18 1986-12-05 Sandoz Sa Nouveaux derives de la 2(1h)-pyridinone, leur preparation et leur utilisation comme medicaments
AT384021B (de) * 1982-05-18 1987-09-25 Sandoz Ag Verfahren zur herstellung neuer 2(1h)-pyridinon- derivate und ihrer salze
FR2529891A1 (fr) * 1982-07-12 1984-01-13 Nativelle Sa Ets Derives du pyridyl-3 alcoxy-5 pyrazole, procede de preparation et application en therapeutique
IT8367883A0 (it) * 1982-08-23 1983-08-22 Rorer Int Overseas Composti cardiotonici del 2 piridone 5 biciclico eteroaril sostituito e relative composizioni farmaceutiche
US4503061A (en) * 1983-07-22 1985-03-05 Warner-Lambert Company Substituted phenyl-pyridinones as cardiotonic agents
IL69407A (en) * 1982-08-23 1987-10-20 Warner Lambert Co 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
US4517192A (en) * 1983-01-31 1985-05-14 Sterling Drug Inc. 6-Alkyl-5-[4-(alkylsulfinyl or alkylsulfonyl)phenyl]-2(1H)-pyridinones and their use as cardiatonics
ES521644A0 (es) * 1983-04-20 1985-10-16 Quimicos Y Farmaceuticos Abel Un nuevo procedimiento para la preparacion de 5-azinil-1,2-dihidroazin-2-onas.
US4568751A (en) * 1983-04-29 1986-02-04 Merrell Dow Pharmaceuticals Inc. 5-Acyl-2-(1H)-pyridinones
DE3406329A1 (de) * 1984-02-22 1985-08-22 Merck Patent Gmbh, 6100 Darmstadt Pyridone
DE3685840D1 (de) 1985-04-30 1992-08-06 Dresden Arzneimittel 3-cyan-pyridine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung.
US5254571A (en) * 1988-04-21 1993-10-19 Smith Kline & French Laboratories Ltd. Chemical compounds

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355278A (en) * 1961-03-13 1967-11-28 Hooker Chemical Corp Herbicidal composition and method
FR2050940A5 (enExample) * 1969-06-30 1971-04-02 Rhone Poulenc Sa
DE2052536A1 (de) * 1969-10-27 1971-05-06 Union Carbide Corp , New York, N Y (VStA) Verfahren zur Herstellung von 2 Pyndonen und deren Derivaten
FR2073341A1 (enExample) * 1969-11-12 1971-10-01 Merck & Co Inc
FR2073342A1 (enExample) * 1969-11-12 1971-10-01 Merck & Co Inc
US3715358A (en) * 1967-12-01 1973-02-06 Merck & Co Inc Method of treating inflammation
FR2327779A1 (fr) * 1975-10-14 1977-05-13 Sterling Drug Inc Pyridinyl-2(1h)-pyridinones et leur preparation
US4038396A (en) * 1975-02-24 1977-07-26 Merck & Co., Inc. Anti-inflammatory oxazole[4,5-b]pyridines

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355278A (en) * 1961-03-13 1967-11-28 Hooker Chemical Corp Herbicidal composition and method
US3715358A (en) * 1967-12-01 1973-02-06 Merck & Co Inc Method of treating inflammation
FR2050940A5 (enExample) * 1969-06-30 1971-04-02 Rhone Poulenc Sa
DE2052536A1 (de) * 1969-10-27 1971-05-06 Union Carbide Corp , New York, N Y (VStA) Verfahren zur Herstellung von 2 Pyndonen und deren Derivaten
FR2073341A1 (enExample) * 1969-11-12 1971-10-01 Merck & Co Inc
FR2073342A1 (enExample) * 1969-11-12 1971-10-01 Merck & Co Inc
US4038396A (en) * 1975-02-24 1977-07-26 Merck & Co., Inc. Anti-inflammatory oxazole[4,5-b]pyridines
FR2327779A1 (fr) * 1975-10-14 1977-05-13 Sterling Drug Inc Pyridinyl-2(1h)-pyridinones et leur preparation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666913A (en) * 1985-11-22 1987-05-19 William H. Rorer, Inc. Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses
US4785005A (en) * 1986-06-25 1988-11-15 Rorer Pharmaceutical Corporation 6-(6-alkylpyridone)-carbostyril compounds and their cardiotonic uses
EP0347027A3 (en) * 1988-04-21 1990-05-23 Smith Kline & French Laboratories Limited Phenylpyridone derivatives,processes for their preparation and pharmaceutical compositions containing them.
EP0428268A3 (en) * 1989-10-13 1991-11-27 Smith Kline & French Laboratories Limited Pharmaceutical phenylpyridone derivatives

Also Published As

Publication number Publication date
DE3106460A1 (de) 1982-01-28
CA1183533A (en) 1985-03-05
IL62246A (en) 1984-09-30
ES8301469A1 (es) 1982-12-01
IT1142458B (it) 1986-10-08
IL62246A0 (en) 1981-05-20
PT72596A (en) 1981-04-01
ES499971A0 (es) 1982-12-01
CH652395A5 (de) 1985-11-15
FR2477148A1 (fr) 1981-09-04
NZ196385A (en) 1983-12-16
FR2477148B1 (enExample) 1983-09-02
GB2070606A (en) 1981-09-09
FI810558A7 (fi) 1981-09-04
PT72596B (en) 1982-07-13
NL8100964A (nl) 1981-10-01
FI810558L (fi) 1981-09-04
YU51581A (en) 1983-12-31
GB2070606B (en) 1984-02-29
DK94481A (da) 1981-09-04
SE8101336L (sv) 1981-09-04
IT8147920A0 (it) 1981-03-02

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AK Designated states

Designated state(s): CH