GB2065642B - 5-(pyridinyl)-2-(1h)-pyridinones useful as cardiotonic agents and their preparation - Google Patents

5-(pyridinyl)-2-(1h)-pyridinones useful as cardiotonic agents and their preparation

Info

Publication number
GB2065642B
GB2065642B GB8037856A GB8037856A GB2065642B GB 2065642 B GB2065642 B GB 2065642B GB 8037856 A GB8037856 A GB 8037856A GB 8037856 A GB8037856 A GB 8037856A GB 2065642 B GB2065642 B GB 2065642B
Authority
GB
United Kingdom
Prior art keywords
pyridinyl
preparation
cardiotonic agents
pyridinones
useful
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.)
Expired
Application number
GB8037856A
Other languages
English (en)
Other versions
GB2065642A (en
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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
Priority claimed from US06/135,100 external-priority patent/US4297360A/en
Priority claimed from US06/198,461 external-priority patent/US4313951A/en
Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB2065642A publication Critical patent/GB2065642A/en
Application granted granted Critical
Publication of GB2065642B publication Critical patent/GB2065642B/en
Expired legal-status Critical Current

Links

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
    • C07D213/78—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
    • C07D213/04—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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic 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
    • C07D213/63—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
    • C07D213/72—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
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon 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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters 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
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
GB8037856A 1979-11-26 1980-11-26 5-(pyridinyl)-2-(1h)-pyridinones useful as cardiotonic agents and their preparation Expired GB2065642B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9750479A 1979-11-26 1979-11-26
US06/135,100 US4297360A (en) 1980-03-28 1980-03-28 5-(Pyridinyl)pyridine-2,3-diamines, preparation thereof and their cardiotonic use
US06/198,461 US4313951A (en) 1979-11-26 1980-10-20 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their cardiotonic use and intermediates therefor
US06/204,726 US4312875A (en) 1980-03-28 1980-11-06 5-(Pyridinyl)-6-(lower-alkyl)-2(1H)-pyridinones, 1,2-dihydro-2-oxo-5-(pyridinyl)-6-(lower-alkyl)nicotinic acids and lower-alkyl esters thereof, and cardiotonic use thereof

Publications (2)

Publication Number Publication Date
GB2065642A GB2065642A (en) 1981-07-01
GB2065642B true GB2065642B (en) 1984-04-04

Family

ID=27492921

Family Applications (2)

Application Number Title Priority Date Filing Date
GB8037856A Expired GB2065642B (en) 1979-11-26 1980-11-26 5-(pyridinyl)-2-(1h)-pyridinones useful as cardiotonic agents and their preparation
GB08315983A Expired GB2131421B (en) 1979-11-26 1983-06-10 Pyridinyl ethenyl alkyl ketones

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB08315983A Expired GB2131421B (en) 1979-11-26 1983-06-10 Pyridinyl ethenyl alkyl ketones

Country Status (20)

Country Link
AT (1) AT379387B (es)
CH (1) CH649535A5 (es)
DE (1) DE3044568A1 (es)
DK (1) DK151799C (es)
ES (1) ES8301920A1 (es)
FI (1) FI76564C (es)
FR (2) FR2470124B1 (es)
GB (2) GB2065642B (es)
GR (1) GR71608B (es)
HK (2) HK31189A (es)
IE (1) IE50632B1 (es)
IL (2) IL61501A (es)
IT (1) IT1148740B (es)
LU (1) LU82957A1 (es)
MX (1) MX155904A (es)
NL (2) NL192202C (es)
NO (2) NO154345C (es)
NZ (1) NZ195564A (es)
PT (1) PT72106B (es)
SE (1) SE442398B (es)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008524233A (ja) * 2004-12-16 2008-07-10 バーテックス ファーマシューティカルズ インコーポレイテッド 炎症性疾患、増殖性疾患および免疫介在性疾患の治療のためのｔｅｃファミリータンパク質キナーゼのインヒビターとして有用なピリド−２−オン
US10493067B2 (en) 2014-12-22 2019-12-03 Cardiora Pty Ltd. Method of treating heart failure with preserved ejection fraction by administering milrinone
US10517833B2 (en) 2011-08-16 2019-12-31 Cardiora Pty Ltd. Uses of milrinone controlled-release formulation

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4305948A (en) * 1980-12-22 1981-12-15 Sterling Drug Inc. N-Hydroxy-1,2-dihydro-2-oxo-5-(pyridinyl)-nicotinimidamide and their cardiotonic use
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
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
IL69407A (en) * 1982-08-23 1987-10-20 Warner Lambert Co 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
IL70169A0 (en) * 1982-11-18 1984-02-29 Sterling Drug Inc 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
GB8414220D0 (en) * 1984-06-04 1984-07-11 Sterwin Ag Medicaments in unit dose form
AU8495091A (en) * 1990-08-21 1992-03-17 Upjohn Company, The Bisphosphonic acid derivatives as anti-arthritic agents
CZ403592A3 (en) * 1992-02-20 1993-12-15 Hoechst Ag Arylcarbonylaminoalkyldihydrooxopyridines, process of their preparation and their use
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
EP2218442A1 (en) 2005-11-09 2010-08-18 CombinatoRx, Inc. Methods, compositions, and kits for the treatment of ophthalmic disorders
MX354786B (es) 2007-06-04 2018-03-21 Synergy Pharmaceuticals Inc Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos.
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
CA2726917C (en) 2008-06-04 2018-06-26 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
WO2010009319A2 (en) 2008-07-16 2010-01-21 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
US9580471B2 (en) 2011-03-01 2017-02-28 Synergy Pharmaceuticals, Inc. Process of preparing guanylate cyclase C agonists
WO2013106547A1 (en) 2012-01-10 2013-07-18 President And Fellows Of Harvard College Beta-cell replication promoting compounds and methods of their use
US9545446B2 (en) 2013-02-25 2017-01-17 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
WO2014151200A2 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
EP2970384A1 (en) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
JP6606491B2 (ja) 2013-06-05 2019-11-13 シナジー ファーマシューティカルズ インコーポレイテッド グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法
JP6694385B2 (ja) 2013-08-09 2020-05-13 アーデリクス，インコーポレーテッド リン酸塩輸送阻害のための化合物及び方法
WO2020237096A1 (en) 2019-05-21 2020-11-26 Ardelyx, Inc. Combination for lowering serum phosphate in a patient

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072746A (en) * 1975-10-14 1978-02-07 Sterling Drug Inc. 3-Amino-5-(pyridinyl)-2(1H)-pyridinones
US4004012A (en) * 1975-10-14 1977-01-18 Sterling Drug Inc. 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008524233A (ja) * 2004-12-16 2008-07-10 バーテックス ファーマシューティカルズ インコーポレイテッド 炎症性疾患、増殖性疾患および免疫介在性疾患の治療のためのｔｅｃファミリータンパク質キナーゼのインヒビターとして有用なピリド−２−オン
JP2009062391A (ja) * 2004-12-16 2009-03-26 Vertex Pharmaceut Inc 炎症性疾患、増殖性疾患および免疫介在性疾患の治療のためのｔｅｃファミリータンパク質キナーゼの阻害物質として有用なピリド−２−オン
US10517833B2 (en) 2011-08-16 2019-12-31 Cardiora Pty Ltd. Uses of milrinone controlled-release formulation
US10736853B2 (en) 2011-08-16 2020-08-11 Cardiora Pty Ltd. Milrinone controlled-release formulation
US11331274B2 (en) 2011-08-16 2022-05-17 Baker Heart and Diabetes Institute Milrinone controlled-release formulation
US10493067B2 (en) 2014-12-22 2019-12-03 Cardiora Pty Ltd. Method of treating heart failure with preserved ejection fraction by administering milrinone
US11291660B2 (en) 2014-12-22 2022-04-05 Baker Heart and Diabetes Institute Method of treating heart failure with preserved ejection fraction by administering milrinone

Also Published As

Publication number Publication date
HK31189A (en) 1989-04-21
GB8315983D0 (en) 1983-07-13
FI76564C (fi) 1988-11-10
CH649535A5 (fr) 1985-05-31
NL970028I2 (nl) 1998-03-02
IL61501A (en) 1984-06-29
NL192202B (nl) 1996-11-01
FR2553767A1 (fr) 1985-04-26
FI803652L (fi) 1981-05-27
DE3044568A1 (de) 1981-08-27
IT8026218A0 (it) 1980-11-25
NL8006399A (nl) 1981-06-16
NO154345C (no) 1986-09-03
FI76564B (fi) 1988-07-29
GB2131421B (en) 1985-06-26
IL69847A0 (en) 1983-12-30
MX155904A (es) 1988-05-23
HK83090A (en) 1990-10-19
PT72106A (fr) 1980-12-01
DK151799C (da) 1988-06-20
NL970028I1 (nl) 1997-10-01
IE802430L (en) 1981-05-26
NO154345B (no) 1986-05-26
SE8008252L (sv) 1981-05-27
DE3044568C2 (es) 1990-11-29
FR2553767B1 (fr) 1987-01-16
NO803550L (no) 1981-05-27
LU82957A1 (fr) 1981-06-04
DK501180A (da) 1981-05-27
ES507620A0 (es) 1982-11-16
IT1148740B (it) 1986-12-03
GB2131421A (en) 1984-06-20
FR2470124B1 (fr) 1986-12-19
NL192202C (nl) 1997-03-04
NZ195564A (en) 1983-09-30
SE442398B (sv) 1985-12-23
FR2470124A1 (fr) 1981-05-29
DK151799B (da) 1988-01-04
IL61501A0 (en) 1981-05-20
ES8301920A1 (es) 1982-11-16
NO156127C (no) 1987-07-29
IE50632B1 (en) 1986-05-28
NO156127B (no) 1987-04-21
AT379387B (de) 1985-12-27
GB2065642A (en) 1981-07-01
PT72106B (fr) 1981-09-29
NO854001L (no) 1981-05-27
GR71608B (es) 1983-06-17
ATA578080A (de) 1985-05-15

Similar Documents

Publication Publication Date Title
GB2065642B (en) 5-(pyridinyl)-2-(1h)-pyridinones useful as cardiotonic agents and their preparation
NZ182270A (en) 5-(pyridinyl)-2-(1h)-pyridinone derivatives and cardiotonic compositions
PH22271A (en) 5-(pyridinyl)pyridine-2,3-diamines, preparation thereof and their cardiotonic use
IL60628A0 (en) Pyrimidinylurea derivatives and their use as herbicides
GB2058059B (en) N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides
IL59443A (en) Phenyl-and pyridylsulfonylureas and-pseudothioureas,their preparation and their use as herbicides
GB2025945B (en) 2-substituted phenoxy-3-chloro-5-trifluoromethyl pyridine compounds and herbicidal compositions thereof
IL60875A0 (en) Benzenesulfonyl-lisoureas and their use as herbicides
NZ193904A (en) Phenoxypyridine derivatives and herbicidal compositions
GB2065475B (en) Compositions for the control of parasites in warm-blooded animals
ZW15280A1 (en) Novel substituted heterocyclic phenoxyamines the method of preparation thereof and the use thereof as local anaestheetics
EG14309A (en) Phenoxy-2-nitrobenzoates useful as herbicides and preparation
GB2065476B (en) Phoshine-generating compositions and their use in controlling pests
NZ195878A (en) 3-acylamino-5-(4(or 3)pyridinyl)-2(1h)-pyridinones and cardiotonic compositions
JPS5620573A (en) Manufacture of 1*22dihydroo22oxoo55 *pyridinyl*nicotinonitrile
ZA807267B (en) 5-(pyridinyl)-2(1h)-pyridinones,useful as cardiotonic agents and their preparation
ZA803679B (en) 5-(4-pyridinyl)-2(lh) pyridinones, useful as cardiotonic agents, and their preparation
BE891493A (fr) Derives de 1,2-dihydro-5(pyridinyl) nicotinamide, leur preparation et leur utilisation comme agents cardiotoniques et intermediaires
GB2047236B (en) 2-hydroxy-benzamide derivatives and use thereof as fungicides
ZA812652B (en) Useful as cardiotonic agents and preparation
PH16741A (en) 5-(pyridinyl)-6-alkyl-2-(1h)-pyridinones and use as cardiotonics
PH16300A (en) Notrothiazoline derivatives and their use as schistosonicidal agents
ZA818897B (en) 5-(pyridinyl)-benzimidazole derivatives and preparation
IL59238A (en) N-substituted alkanesulfoanilides and their use as herbicides
EG14983A (en) Method of preparing 5-(pyridinyl)-2(1h)-pyridimones useful as cardiatonic agents

Legal Events

Date Code Title Description
CTFF Supplementary protection certificate filed

Free format text: SPC/GB93/128, 930630

CTFG Supplementary protection certificate granted

Free format text: SPC/GB93/128, 940325, EXPIRES:20021015

732E Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)
CTFE Supplementary protection certificate entered into force

Free format text: SPC/GB93/128, 20001126, EXPIRES: 20021015

PE20 Patent expired after termination of 20 years

Effective date: 20001125

SPCE Supplementary protection certificate expired

Spc suppl protection certif: SPC/GB93/128

Expiry date: 20021015