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6-(acylaminoaryl)-3(2H)-pyridazinone derivatives and their use

Assignee: BASF SE
•
Filing: 1984-01-17
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Granted: 1987-01-13
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Expires: 2004-01-17
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Abstract

Abstract Novel 6-(acylaminoaryl)-3(2H)-pyridazinones of the formula <IMAGE> (I) where R1, R2, R3, R4, A and B have the meanings given in the description, and their preparation are described and inhibiting thrombocyte aggregation and gastric secretion. The compounds are useful for treating disorders.

Inventors

  • 👤 Phillip A. Rossy
  • 👤 Marco Thyes
  • 👤 Albrecht Franke
  • 👤 Horst Koenig
  • 👤 Hans Dieter Lehmann
  • 👤 Josef Gries
  • 👤 Ludwig Friedrich
  • 👤 Dieter Lenke

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 00:09
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P1/00; A61P1/04; A61P7/00; A61P7/02; A61P9/00; A61P9/12; C07D233/00; C07D233/54; C07D233/56; C07D237/00; C07D237/02; C07D237/04; C07D237/06; C07D237/10; C07D237/14; C07D237/26; C07D249/00; C07D249/02; C07D249/08; C07D401/00; C07D401/02; C07D401/12; C07D401/14; C07D403/00; C07D403/02; C07D403/12; C07D405/00; C07D405/02; C07D405/12; C07D413/00; C07D413/02; C07D413/12

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 576 words
A 6-(alkanoylaminoaryl)-3(2H)-pyridazinone derivative of the formula I ##STR558## wherein the substituents on the phenylene radical are para to one another, A and B are each hydrogen or together form a bond, R 1 is hydrogen or methyl, R 2 is hydrogen or, where A and B are each hydrogen R 1 and R 2 together form a C 1 -C 2 -alkylene radical, R 3 is a straight-chain C 1 -C 4 -alkylene group which can be substituted by C 1 -C 3 -alkyl group or by two methyl groups, and R 4 is (b) a group of the formula II ##STR559## where the broken line can be an additional bond, R 5 is C 1 -C 4 -alkyl which is unsubstituted or substituted by phenyl, or phenyl which is unsubstituted or substituted by 1 or 2 halogen atoms, or is a group of the formula R 7 R 8 N, where R 7 is hydrogen or phenyl, and R 8 is C 1 -C 4 -acyl or benzoyl, or R 7 and R 8 , together with the nitrogen atom, form a benzimidazol-2-on-1-yl group, R 6 is C 1 -C 4 -alkyl, hydroxyl, C 1 -C 4 -acyl, (C 1 -C 5 -alkoxy)-carbonyl or cyano, or R 5 and R 6 together form a C 1 -C 4 -alkylene chain, and m is 0, 1 or 2, or (c) a group of the formula III ##STR560## `where R 9 is a C 1 -C 3 -hydrocarbon radical which may be substituted by phenyl or a C 3 -C 8 -cycloalkyl (in which case a C 5 -C 8 -cycloalkyl group can be benzofused) or C 6 -C 10 -aryl which can contain 1 to 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, nitro, hydroxyl, C 1 -C 4 -acyl, carboxyl, (C 1 -C 5 -alkoxy)-carbonyl, amido, N-(C 1 -C 4 -alkyl)amido, N,N-di-(C 1 -C 4 -alkyl)amido, tri(C 1 -C 4 -alkyl)-silyl, cyano, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkanoyl amino groups and/or halogen atoms; a C 6 -C 10 -aroyl group which is unsubstituted or substituted by 1 to 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, nitro, hydroxyl, C 1 -C 4 -alkanoyl, carboxyl, C 1 -C 5 -alkoxy-carbonyl, N,N-di-(C 1 -C 4 -alkyl)-amido, cyano, di-(C 1 -C 4 -alkyl)-amino groups and/or halogen atoms; or a hetaroyl group having 5 to 6 ring members, which can contain 1 to 3 hetero atoms and may be benzofused; a C 3 -C 12 -cycloalkyl, C 1 -C 8 -acyl or (C 1 -C 5 -alkoxy)-carbonyl group or a C 6 -C 10 -aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, hydroxyl, trifluoromethyl, C 1 -C 4 -acyl, carboxyl, (C 1 -C 5 -alkoxy)-carbonyl, cyano, nitro, amino, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, arylamino or C 1 -C 4 -acylamino; or a 5-membered or 6-membered hetaryl radical which may be benzofused, contains 1 to 3 nitrogen atoms and may or may not contain an oxygen atom or sulfur atom, and p is 2 or 3, or (e) a group of the formula V ##STR561## where R 12 and R 13 are each hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and n is 1, 2, or 3.
Claim 2
Dependent Claim 576 words
A 6-(alkanoylaminoaryl)-3(2H)-pyridazinone derivative of the formula I ##STR558## wherein the substituents on the phenylene radical are para to one another, A and B are each hydrogen or together form a bond, R 1 is hydrogen or methyl, R 2 is hydrogen or, where A and B are each hydrogen R 1 and R 2 together form a C 1 -C 2 -alkylene radical, R 3 is a straight-chain C 1 -C 4 -alkylene group which can be substituted by C 1 -C 3 -alkyl group or by two methyl groups, and R 4 is (b) a group of the formula II ##STR559## where the broken line can be an additional bond, R 5 is C 1 -C 4 -alkyl which is unsubstituted or substituted by phenyl, or phenyl which is unsubstituted or substituted by 1 or 2 halogen atoms, or is a group of the formula R 7 R 8 N, where R 7 is hydrogen or phenyl, and R 8 is C 1 -C 4 -acyl or benzoyl, or R 7 and R 8 , together with the nitrogen atom, form a benzimidazol-2-on-1-yl group, R 6 is C 1 -C 4 -alkyl, hydroxyl, C 1 -C 4 -acyl, (C 1 -C 5 -alkoxy)-carbonyl or cyano, or R 5 and R 6 together form a C 1 -C 4 -alkylene chain, and m is 0, 1 or 2, or (c) a group of the formula III ##STR560## `where R 9 is a C 1 -C 3 -hydrocarbon radical which may be substituted by phenyl or a C 3 -C 8 -cycloalkyl (in which case a C 5 -C 8 -cycloalkyl group can be benzofused) or C 6 -C 10 -aryl which can contain 1 to 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, nitro, hydroxyl, C 1 -C 4 -acyl, carboxyl, (C 1 -C 5 -alkoxy)-carbonyl, amido, N-(C 1 -C 4 -alkyl)amido, N,N-di-(C 1 -C 4 -alkyl)amido, tri(C 1 -C 4 -alkyl)-silyl, cyano, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkanoyl amino groups and/or halogen atoms; a C 6 -C 10 -aroyl group which is unsubstituted or substituted by 1 to 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, nitro, hydroxyl, C 1 -C 4 -alkanoyl, carboxyl, C 1 -C 5 -alkoxy-carbonyl, N,N-di-(C 1 -C 4 -alkyl)-amido, cyano, di-(C 1 -C 4 -alkyl)-amino groups and/or halogen atoms; or a hetaroyl group having 5 to 6 ring members, which can contain 1 to 3 hetero atoms and may be benzofused; a C 3 -C 12 -cycloalkyl, C 1 -C 8 -acyl or (C 1 -C 5 -alkoxy)-carbonyl group or a C 6 -C 10 -aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, hydroxyl, trifluoromethyl, C 1 -C 4 -acyl, carboxyl, (C 1 -C 5 -alkoxy)-carbonyl, cyano, nitro, amino, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, arylamino or C 1 -C 4 -acylamino; or a 5-membered or 6-membered hetaryl radical which may be benzofused, contains 1 to 3 nitrogen atoms and may or may not contain an oxygen atom or sulfur atom, and p is 2 or 3, or (e) a group of the formula V ##STR561## where R 12 and R 13 are each hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and n is 1, 2, or 3.
Claim 3
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperazino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 4
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperazino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 5
Dependent Claim 1 words
6-{p-[3-(4-Pyrid-2-yl-1-piperazino)-propionyl-amino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 6
Dependent Claim 1 words
6-{p-[3-(4-Pyrid-2-yl-1-piperazino)-propionyl-amino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 7
Dependent Claim 1 words
6-{p-[3-(4-Benzyl-1-piperazino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 8
Dependent Claim 1 words
6-{p-[3-(4-Benzyl-1-piperazino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 9
Dependent Claim 1 words
6-{p-[2-(4-Phenyl-1-piperidino)-acetylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 10
Dependent Claim 1 words
6-{p-[2-(4-Phenyl-1-piperidino)-acetylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 11
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-4,5-dihydropyridazinone.
Claim 12
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-4,5-dihydropyridazinone.
Claim 13
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-5-methyl-4,5-dihydropyridazinone.
Claim 14
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-5-methyl-4,5-dihydropyridazinone.
Claim 15
Dependent Claim 1 words
2-{p-[3-(4-Phenyl-1-piperidino)-propynylamino]-phenyl}-3,4-diazabicyclo[4.1.0]hept-2-en-5-one.
Claim 16
Dependent Claim 1 words
2-{p-[3-(4-Phenyl-1-piperidino)-propynylamino]-phenyl}-3,4-diazabicyclo[4.1.0]hept-2-en-5-one.
Claim 17
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-(1,2,3,6-tetrahydropyridino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 18
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-(1,2,3,6-tetrahydropyridino)-propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 19
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-3(2H)-pyridazinone.
Claim 20
Dependent Claim 1 words
6-{p-[3-(4-Phenyl-1-piperidino)-propionylamino]-phenyl}-3(2H)-pyridazinone.
Claim 21
Dependent Claim 1 words
6-{p-[3-(1-(1,2,3,4-Tetrahydroisoquinolino)propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 22
Dependent Claim 1 words
6-{p-[3-(1-(1,2,3,4-Tetrahydroisoquinolino)propionylamino]-phenyl}-5-methyl-4,5-dihydro-3(2H)-pyridazinone.
Claim 23
Dependent Claim 24 words
A therapeutic composition comprising a pharmaceutical excipient and an effective amount of a 6-(alkanoyl-aminoaryl)-3(2H)-pyridazinone derivative as claimed in claim 16 as the active compound.
Claim 24
Dependent Claim 29 words
The method of treating disease caused by thrombocyte aggregation in a patient suffering therefrom which comprises administering an effective amount of a 6-(alkanoyl-aminoaryl)-3(2H)-pyridazinone derivative as claimed in claim 12.

References Cited (Backward Citations)

US3824271A Cited
US3888901A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-01-12 1990-07-14 1991-01-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-01-12 1994-07-14 1995-01-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-01-12 1998-07-14 1999-01-13 $7700.00 Window Closed / Lapsed

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