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

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84Nitriles
    • C07D213/85Nitriles in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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
    • C07D213/44Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46Oxygen atoms
    • C07D213/50Ketonic radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/63One oxygen atom
    • C07D213/64One oxygen atom attached in position 2 or 6
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/73Unsubstituted amino or imino radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/74Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/80Acids; Esters in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic 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 (de)
CH (1) CH649535A5 (de)
DE (1) DE3044568A1 (de)
DK (1) DK151799C (de)
ES (1) ES507620A0 (de)
FI (1) FI76564C (de)
FR (2) FR2470124B1 (de)
GB (2) GB2065642B (de)
GR (1) GR71608B (de)
HK (2) HK31189A (de)
IE (1) IE50632B1 (de)
IL (2) IL61501A (de)
IT (1) IT1148740B (de)
LU (1) LU82957A1 (de)
MX (1) MX155904A (de)
NL (2) NL192202C (de)
NO (2) NO154345C (de)
NZ (1) NZ195564A (de)
PT (1) PT72106B (de)
SE (1) SE442398B (de)

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
WO1992003451A1 (en) * 1990-08-21 1992-03-05 The Upjohn Company 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 (de) 2005-11-09 2010-08-18 CombinatoRx, Inc. Verfahren, Zusammensetzungen und Kits zur Behandlung von ophthalmologischen Erkrankungen
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
WO2008151257A2 (en) 2007-06-04 2008-12-11 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP2328910B1 (de) 2008-06-04 2014-08-06 Synergy Pharmaceuticals Inc. Für die behandlung von gastrointestinalen erkrankungen, entzündungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase
AU2009270833B2 (en) 2008-07-16 2015-02-19 Bausch Health Ireland Limited 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
CA3100941C (en) 2011-03-01 2024-03-05 Synergy Pharmaceuticals Inc. Process of preparing guanylate cyclase c agonists
US20150119399A1 (en) 2012-01-10 2015-04-30 President And Fellows Of Harvard College Beta-cell replication promoting compounds and methods of their use
JP6499591B2 (ja) 2013-02-25 2019-04-10 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 結腸洗浄において用いるためのグアニル酸シクラーゼ受容体アゴニスト
EP2968439A2 (de) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Zusammensetzungen zur behandlung von magen-darm-störungen
CA2905438A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
US10011637B2 (en) 2013-06-05 2018-07-03 Synergy Pharmaceuticals, Inc. Ultra-pure agonists of guanylate cyclase C, method of making and using same
KR102456567B1 (ko) 2013-08-09 2022-10-19 알데릭스, 인코포레이티드 인산염 수송을 억제하기 위한 화합물 및 방법
EP3972599A1 (de) 2019-05-21 2022-03-30 Ardelyx, Inc. Kombination zur senkung des serum-phosphatspiegels bei einem patienten

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

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
IL60628A0 (en) Pyrimidinylurea derivatives and their use as herbicides
GB2058059B (en) N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides
NZ189728A (en) Pyridine derivatives and herbicidal compositions
IL59443A (en) Phenyl-and pyridylsulfonylureas and-pseudothioureas,their preparation and their use as herbicides
NZ189639A (en) Pyridine derivatives and herbicidal compositions
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
DE3379788D1 (en) 2(1h)-pyridinones, useful as cardiotonic agents, and their production
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
PT71427A (en) Process for the preparation of 5-(4-pyridinyl)-2 (1h) pyridinones useful as cardiotonic agents
BE891493A (fr) Derives de 1,2-dihydro-5(pyridinyl) nicotinamide, leur preparation et leur utilisation comme agents cardiotoniques et intermediaires
ZA812652B (en) Useful as cardiotonic agents and preparation
ZA818897B (en) 5-(pyridinyl)-benzimidazole derivatives and preparation
IL59238A (en) N-substituted alkanesulfoanilides and their use as herbicides
JPS5686173A (en) 11isopropyll44phenyll2*1h**quinazolinone derivative
AU536354B2 (en) 5-(pyridinyl)-2(1h)-pyridinones

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