FI76564C - Förfarande för framställning av terapeutiskt användbara 2(1H)-pyridino ner - Google Patents

Förfarande för framställning av terapeutiskt användbara 2(1H)-pyridino ner Download PDF

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Publication number
FI76564C
FI76564C FI803652A FI803652A FI76564C FI 76564 C FI76564 C FI 76564C FI 803652 A FI803652 A FI 803652A FI 803652 A FI803652 A FI 803652A FI 76564 C FI76564 C FI 76564C
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Finland
Prior art keywords
pyridinyl
methyl
compound
formula
pyridinone
Prior art date
Application number
FI803652A
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English (en)
Finnish (fi)
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FI76564B (fi
FI803652L (fi
Inventor
Richard Everett Philion
George Yohe Lesher
Donald Frederick Page
Chester Joseph Opalka Jr
Original Assignee
Sterling Drug Inc
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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 FI803652L publication Critical patent/FI803652L/fi
Priority to FI854740A priority Critical patent/FI77851C/sv
Application granted granted Critical
Publication of FI76564B publication Critical patent/FI76564B/fi
Publication of FI76564C publication Critical patent/FI76564C/sv

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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
    • C07D213/78—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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (3)

1. Förfarande för framställning av en terapeutiskt användbar 2(1H)-pyridinon med formeln "rr R N ^ ^ 0 10 j R! väri Q är väte, amino, cyan, karbamyl, halogen, lägre alkylamino, di(lägre alkyl) amino, alkanoylamino eller 15 acetoxisubstituerad alkanoylamino, karboxi eller lägre alkoxikarbonyl, R^ är väte eller lägre alkyl R är lägre alkyl och PY är 4-, 3- eller 2- pyridinyl eller 4-, 3- eller 2-pyridinyl med en eller tvä lägre alkylsubstituenter, eller ett syraadditions-20 eller katjoniskt sait därav, kännetecknat därav, att a) en förening med formeln R3R4NCH=C-C(=0)-R III 25 pY väri Rj och R^ vardera är lägre alkyl, bringas att reage-ra med malonamid tili en förening med formeln I, väri Q 30 är karbamyl, eller b) en förening med formeln III som ovan definie-rats bringas att reagera med N-R^-Ot-cyanacetamid tili en förening med formeln I, väri Q är cyan, och ifall önsvärt, en erhällen förening med formeln I, väri Q är cyan, par-35 tiellt hydrolyseras tili motsvarande förening, väri Q är karbamyl; och ifall önskvärt, en medelst förfarande a) eller b) erhällen förening med formeln I omvandlas tili en annan förening med formeln I genom att utföra en eller 56 7 6 5 6 4 eller flera av följande ätgärder: i) en förening med formeIn I, väri Q är karbamyl, bringas att reagera med en reaktant som är kapabel att omvandla karbamyl tili amino, för erhällande av motsva- 5 rande förening, väri Q är amino; ii) en förening med formeln I, väri Q är amino, bringas att reagera med en eller tvä molekylvikter av ett lägre alkyleringsämne tili motsvarande förening, väri Q pä motsvarande sätt är lägre alkylamino eller di(lägre 10 alkyl)amino; iii) förening med formeln I, väri Q är amino, bringas att reagera med ett lägre acyleringsämne tili motsvarande förening, väri Q är lägre acylamino; iv) en förening med formeln I, väri Q är cyan, 15 hydrolyseras tili motsvarande förening, väri Q är karboxi; v) en förening med formeln I, väri Q är cyan eller karboxi, uppvärms tillsammans med en vattenlösning av en mineralsyra tili motsvarande förening, väri Q är väte; 20 vi) en förening med formeln I, väri Q är karboxi, förestras med en lägre alkanolförening tili motsvarande förening, väri Q är lägre alkoxikarbonyl; vii) en förening med formeln I, väri Q är väte, bringas att reagera med halogen till motsvarande förening, 25 väri Q är halogen; viii) en förening med formeln I, väri Q är halogen, bringas att reagera med lägre alkylamin eller di-(lägre alkyl)amin tili motsvarande förening, väri Q pä motsvarande sätt är lägre alkylamino eller di(lägre alkyl)- 30 amino; och ix) en erhällen fri bas omvandlas tili ett syra-additionssalt därav, eller en erhällen förening omvandlas tili et katjoniskt sait därav.
2. Förfarande enligt patentkravet 1, k ä n n e - 35 tecknat därav, att man väljer utgängsföreningar, väri R är metyl eller etyl och PY är 4-pyridinyl.
FI803652A 1979-11-26 1980-11-24 Förfarande för framställning av terapeutiskt användbara 2(1H)-pyridino ner FI76564C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI854740A FI77851C (sv) 1979-11-26 1985-11-29 1-pyridinyl-2-(dialkylamino)etenylalkylketoner.

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US9750479A 1979-11-26 1979-11-26
US9750479 1979-11-26
US13510080 1980-03-28
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
US19846180 1980-10-20
US20472680 1980-11-06
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 (3)

Publication Number Publication Date
FI803652L FI803652L (fi) 1981-05-27
FI76564B FI76564B (fi) 1988-07-29
FI76564C true FI76564C (sv) 1988-11-10

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Application Number Title Priority Date Filing Date
FI803652A FI76564C (sv) 1979-11-26 1980-11-24 Förfarande för framställning av terapeutiskt användbara 2(1H)-pyridino ner

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AT (1) AT379387B (sv)
CH (1) CH649535A5 (sv)
DE (1) DE3044568A1 (sv)
DK (1) DK151799C (sv)
ES (1) ES507620A0 (sv)
FI (1) FI76564C (sv)
FR (2) FR2470124B1 (sv)
GB (2) GB2065642B (sv)
GR (1) GR71608B (sv)
HK (2) HK31189A (sv)
IE (1) IE50632B1 (sv)
IL (2) IL61501A (sv)
IT (1) IT1148740B (sv)
LU (1) LU82957A1 (sv)
MX (1) MX155904A (sv)
NL (2) NL192202C (sv)
NO (2) NO154345C (sv)
NZ (1) NZ195564A (sv)
PT (1) PT72106B (sv)
SE (1) SE442398B (sv)

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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
JPH06500112A (ja) * 1990-08-21 1994-01-06 ジ・アップジョン・カンパニー 抗関節炎剤としてのビスホスホン酸誘導体
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
MX2007007330A (es) * 2004-12-16 2007-10-04 Vertex Pharma Piridonas de utilidad como inhibidores de quinasas .
NZ568694A (en) 2005-11-09 2011-09-30 Zalicus Inc Method, compositions, and kits for the treatment of medical conditions
US7879802B2 (en) 2007-06-04 2011-02-01 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
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
EP3239170B1 (en) 2008-06-04 2019-03-20 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP3241839B1 (en) 2008-07-16 2019-09-04 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
CN108676076A (zh) 2011-03-01 2018-10-19 辛纳吉制药公司 制备鸟苷酸环化酶c激动剂的方法
EP2744496A4 (en) 2011-08-16 2015-04-08 Baker Idi Heart And Diabetes Inst Holdings Ltd FORMULATIONS WITH TAXED RELEASE
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US4004012A (en) * 1975-10-14 1977-01-18 Sterling Drug Inc. 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones
US4072746A (en) * 1975-10-14 1978-02-07 Sterling Drug Inc. 3-Amino-5-(pyridinyl)-2(1H)-pyridinones

Also Published As

Publication number Publication date
DK151799C (da) 1988-06-20
NL192202B (nl) 1996-11-01
IL61501A (en) 1984-06-29
GB8315983D0 (en) 1983-07-13
NL8006399A (nl) 1981-06-16
NO854001L (no) 1981-05-27
AT379387B (de) 1985-12-27
NZ195564A (en) 1983-09-30
LU82957A1 (fr) 1981-06-04
DK151799B (da) 1988-01-04
GB2065642B (en) 1984-04-04
IE802430L (en) 1981-05-26
FR2553767A1 (fr) 1985-04-26
DE3044568C2 (sv) 1990-11-29
DK501180A (da) 1981-05-27
IL61501A0 (en) 1981-05-20
FR2470124A1 (fr) 1981-05-29
NL970028I2 (nl) 1998-03-02
NO156127C (no) 1987-07-29
SE442398B (sv) 1985-12-23
IL69847A0 (en) 1983-12-30
NO156127B (no) 1987-04-21
IT8026218A0 (it) 1980-11-25
ES8301920A1 (es) 1982-11-16
GB2131421B (en) 1985-06-26
NL192202C (nl) 1997-03-04
PT72106B (fr) 1981-09-29
HK31189A (en) 1989-04-21
FI76564B (fi) 1988-07-29
ES507620A0 (es) 1982-11-16
GB2131421A (en) 1984-06-20
HK83090A (en) 1990-10-19
NO803550L (no) 1981-05-27
ATA578080A (de) 1985-05-15
IE50632B1 (en) 1986-05-28
NO154345C (no) 1986-09-03
GB2065642A (en) 1981-07-01
SE8008252L (sv) 1981-05-27
PT72106A (fr) 1980-12-01
CH649535A5 (fr) 1985-05-31
FR2553767B1 (fr) 1987-01-16
DE3044568A1 (de) 1981-08-27
IT1148740B (it) 1986-12-03
NL970028I1 (nl) 1997-10-01
MX155904A (es) 1988-05-23
FI803652L (fi) 1981-05-27
FR2470124B1 (fr) 1986-12-19
GR71608B (sv) 1983-06-17
NO154345B (no) 1986-05-26

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