LU83320A1 - 4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques - Google Patents

4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques Download PDF

Info

Publication number: LU83320A1
Authority: LU; Luxembourg
Prior art keywords: pyridinyl; methyl; dihydro; pyridazinone; acid
Prior art date: 1980-04-28

Application number

LU83320A

Other languages

English (en)

French (fr)

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.)

1980-04-28

Filing date

1981-04-28

Publication date

1981-12-01

1981-03-13 Priority claimed from US06/243,472 external-priority patent/US4337253A/en

1981-03-18 Priority claimed from US06/245,086 external-priority patent/US4486431A/en

1981-04-28 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1981-12-01 Publication of LU83320A1 publication Critical patent/LU83320A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 11
239000000496 cardiotonic agent Substances 0.000 title description 7
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
-1 3-pyridinyl group Chemical group 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 33
238000000034 method Methods 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 21
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
239000012458 free base Substances 0.000 claims description 8
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
WNDHJGIIUPAEBD-UHFFFAOYSA-N 5-methyl-3-pyridin-4-yl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)CC(C=2C=CN=CC=2)=N1 WNDHJGIIUPAEBD-UHFFFAOYSA-N 0.000 claims description 6
230000003177 cardiotonic effect Effects 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
230000000747 cardiac effect Effects 0.000 claims description 4
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AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
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UTISRGMYIPHHBR-UHFFFAOYSA-N 4-oxo-4-pyridin-4-ylbutanenitrile Chemical compound N#CCCC(=O)C1=CC=NC=C1 UTISRGMYIPHHBR-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
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239000002220 antihypertensive agent Substances 0.000 description 3
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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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
- C07D213/24—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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles

Landscapes

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

LU83320A 1980-04-28 1981-04-28 4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques LU83320A1 (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US14456480A	1980-04-28	1980-04-28
US14456480		1980-04-28
US06/243,472 US4337253A (en)	1980-04-28	1981-03-13	4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic
US24347281		1981-03-13
US24508681		1981-03-18
US06/245,086 US4486431A (en)	1981-01-14	1981-03-18	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones

Publications (1)

Publication Number	Publication Date
LU83320A1 true LU83320A1 (fr)	1981-12-01

Family

ID=27386124

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU83320A LU83320A1 (fr)	1980-04-28	1981-04-28	4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques

Country Status (15)

Country	Link
AT (1)	ATA190481A (de)
DE (1)	DE3116791A1 (de)
DK (1)	DK186781A (de)
ES (1)	ES8203880A1 (de)
FR (1)	FR2481282A1 (de)
GB (1)	GB2076807B (de)
IL (1)	IL62679A0 (de)
IT (1)	IT1137465B (de)
LU (1)	LU83320A1 (de)
NL (1)	NL8102078A (de)
NO (1)	NO811421L (de)
NZ (1)	NZ196889A (de)
PH (1)	PH16845A (de)
PT (1)	PT72936B (de)
SE (1)	SE8102661L (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4304777A (en) *	1979-08-30	1981-12-08	Sterling Drug Inc.	6-(Pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics

1981
- 1981-04-17 IL IL62679A patent/IL62679A0/xx unknown
- 1981-04-22 NZ NZ196889A patent/NZ196889A/en unknown
- 1981-04-23 GB GB8112639A patent/GB2076807B/en not_active Expired
- 1981-04-24 FR FR8108252A patent/FR2481282A1/fr not_active Withdrawn
- 1981-04-27 NO NO811421A patent/NO811421L/no unknown
- 1981-04-27 ES ES501666A patent/ES8203880A1/es not_active Expired
- 1981-04-27 PH PH25564A patent/PH16845A/en unknown
- 1981-04-27 IT IT21384/81A patent/IT1137465B/it active
- 1981-04-27 SE SE8102661A patent/SE8102661L/xx not_active Application Discontinuation
- 1981-04-27 PT PT72936A patent/PT72936B/pt unknown
- 1981-04-27 DK DK186781A patent/DK186781A/da not_active Application Discontinuation
- 1981-04-28 NL NL8102078A patent/NL8102078A/nl not_active Application Discontinuation
- 1981-04-28 LU LU83320A patent/LU83320A1/fr unknown
- 1981-04-28 AT AT811904A patent/ATA190481A/de not_active IP Right Cessation
- 1981-04-28 DE DE19813116791 patent/DE3116791A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
SE8102661L (sv)	1981-10-29
NL8102078A (nl)	1981-11-16
NO811421L (no)	1981-10-29
ES501666A0 (es)	1982-04-01
IT1137465B (it)	1986-09-10
GB2076807B (en)	1984-03-14
NZ196889A (en)	1984-04-27
IL62679A0 (en)	1981-06-29
DE3116791A1 (de)	1982-04-15
GB2076807A (en)	1981-12-09
ES8203880A1 (es)	1982-04-01
IT8121384A0 (it)	1981-04-27
DK186781A (da)	1981-10-29
FR2481282A1 (fr)	1981-10-30
PH16845A (en)	1984-03-19
PT72936A (en)	1981-05-01
ATA190481A (de)	1983-12-15
PT72936B (en)	1982-04-12

Publication	Publication Date	Title
CH619936A5 (de)	1980-10-31
FR2553767A1 (fr)	1985-04-26	1-pyridinyl-2-(dialkyl-amino) ethenyl alkyl cetones et leur procede de preparation
LU82728A1 (fr)	1981-03-24	6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique
FR2479225A1 (fr)	1981-10-02	Imidazopyridines, leur preparation et leur utilisation comme agents cardiotoniques
EP0114850B1 (de)	1988-06-29	Substituierte 2,5-diamino 1,4-diazole, verfahren zu ihrer herstellung, und diese enthaltende farmazeutische zusammenstellungen
FR2478100A1 (fr)	1981-09-18	Derives de pyrazolopyridine, leur preparation et leur utilisation comme agents cardiotoniques
EP0231709A2 (de)	1987-08-12	Phenylnaphthyridine mit einer funktionellen Gruppe in Position 3, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel besonders als Anti-Ulcus
LU83320A1 (fr)	1981-12-01	4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques
JPH05502235A (ja)	1993-04-22	イミダゾール類
US4985427A (en)	1991-01-15	Triazine derivatives
LU82997A1 (fr)	1981-07-23	6-(pyridinyl)-pyridazines,leur preparation et leur utilisation therapeutique
US4337253A (en)	1982-06-29	4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic
LU83032A1 (fr)	1981-07-23	3-acylamino-5(pyridinyl)-2(1h)-pyridinones,leur preparation et leur utilisation comme agents cardiotoniques
EP1023287B1 (de)	2002-06-12	3-oxo-2(h)-1,2,4-triazinderivate als 5ht1a rezeptor liganden
US4486431A (en)	1984-12-04	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones
FR2496659A1 (fr)	1982-06-25	Derives de 1,2 dihydro-5(pyridinyl)nicotinamide, leur preparation et leur utilisation comme agents cardiotoniques et intermediaires
BE884859A (fr)	1981-02-23	6-(pyridinyl)-3 (2h)pyridazinones, leur preparation et leur utilisation therapeutique
CA1211441A (fr)	1986-09-16	Procede de preparation de nouvelles piperidinoguanidines substituees, et des compositions pharmaceutiques en renfermant
FR2706898A1 (de)	1994-12-30
LU83396A1 (fr)	1982-01-20	Compositions cardiotoniques contenant des aminophenylpyridines,nouvelles aminophenylpyridines et leur preparation
CA1166255A (en)	1984-04-24	4,5-dihydro-2-substituted-6-(pyridinyl)-3(2h)- pyridazinones, preparation and cardiotonic use thereof
JPH01168683A (ja)	1989-07-04	新規な置換ニトロジヒドロピリジン、その製造法、及びその使用
US4632924A (en)	1986-12-30	5-(4-substituted)phenyl-2-pyrazinones
FR2601364A1 (fr)	1988-01-15	Nouveaux derives de la piperazine dione-2,6, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
FR2508904A2 (fr)	1983-01-07	Nouveaux composes heterocycliques azotes anti-inflammatoires et immunoregulateurs et composition pharmaceutique les contenant