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EP0138490A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

4-alkyl methylenedioxy-2-1[H]-quinazolinones

Assignee: Ortho Pharmaceutical Corp
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Filing: 1984-09-28
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Granted: —
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Expires: 2004-09-28
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Abstract

Abstract 4-Alkyl-5,6,-, 6,7-methylenedioxy-2-1[H]-quinazolinones are prepared from 2,3-methylenedioxyacetophenones. The 4-alkyt-5,6-,6,7-methylonodioxy-2-1 [H]-quinazolinones are active as cardiotonic agents.

Inventors

  • 👤 Victor T. Bandurco
  • 👤 Stanley C. Bell
  • 👤 Donald W. Combs
  • 👤 Robert Falotico

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-04 07:20
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; A; A61; A61P; A61P9/00; A61P9/04; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/54; C07D317/58

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 20 words
A compound of the formula: wherein R is hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 20 words
A compound of the formula: wherein R is hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 8 words
The compound of Claim 1 which is 5,6-methylenedioxy-4-methyl-2-l[H]-quinazolinone.
Claim 4
Dependent Claim 8 words
The compound of Claim 1 which is 5,6-methylenedioxy-4-ethyl-2-1[H]-quinazolinone.
Claim 5
Dependent Claim 8 words
The compound of Claim 1 which is 5,6-methylenedioxy-2-l[H]-quinazolinone.
Claim 6
Dependent Claim 8 words
The compound of Claim 1 which is 6,7-methylenedioxy-4-methyl-2-1[H]-quinazolinone.
Claim 7
Dependent Claim 8 words
The compound of Claim 1 which is 6,7-methylenedioxy-4-ethyl-2-1[H]-quinazolinone.
Claim 8
Dependent Claim 8 words
The compound of Claim 1 which is 6,7-methyleneaioxy-2-l[H]-quinazolinone.
Claim 9
Dependent Claim 71 words
The process for preparing a compound of Claim 1 of the formula: wherein R is lower alkyl, which comprises reacting a compound of the formula: with nitric acid to form the corresponding nitro compound, reducing the nitro compound intermediate with a reducing agent to form an aminoketone of the formula: reacting the aninoketone with a cyanate in the presence of an acid, and neutralizing the reaction mixture with a mild base.
Claim 10
Dependent Claim 12 words
The process of Claim 8 wherein the reducing agent is ferrous sulfate.
Claim 11
Dependent Claim 14 words
or Claim 9 10. The process of Claim 8/wherein the cyanate is potassium cyanate.
Claim 12
Dependent Claim 13 words
any of to 10 11. The process of/Clairs8/wherein the acid is acetic acid.
Claim 13
Dependent Claim 13 words
any of to 10 11. The process of/Clairs8/wherein the acid is acetic acid.
Claim 14
Dependent Claim 15 words
any of to 11 12. The process of/Clains 8/wherein the mild base is ammonium hydroxide.
Claim 15
Dependent Claim 15 words
any of to 11 12. The process of/Clains 8/wherein the mild base is ammonium hydroxide.
Claim 16
Dependent Claim 42 words
The process for preparing a compound of the formula: wherein R is hydrogen or lower alkyl, which comprises reacting a compound of the formula: with a cyanate in the presence of an acid and neutralizing the reaction mixture with a mild base.
Claim 17
Dependent Claim 42 words
The process for preparing a compound of the formula: wherein R is hydrogen or lower alkyl, which comprises reacting a compound of the formula: with a cyanate in the presence of an acid and neutralizing the reaction mixture with a mild base.
Claim 18
Dependent Claim 18 words
The process of Claim 13 wherein the cyanate is potassium cyanate and the reducing agent is ferrous sulfate.
Claim 19
Dependent Claim 14 words
or Claim 14 15. The process of Claim 13/wherein the acid is acetic acid.
Claim 20
Dependent Claim 13 words
any of to 15 16. The process of/Claimsl3/wherein the base is ammonium hydroxide.
Claim 21
Dependent Claim 77 words
The process for preparing a compound of the formula: which comprises reacting a compound of the formula: with ethylene glycol to form a compound of the formula: reducing the nitro compound with a reducing agent to form an amine of the formula: reacting the amino compound with an alkylhaloformate to form a 2-carboalkoxyamino-5,6-methylene-dioxybenzaldehyde, reacting the 2-carboalkoxyamino compound with an anmonium salt in the present of an organic acid, and neutralizing the reaction mixture with a mild base.
Claim 22
Dependent Claim 77 words
The process for preparing a compound of the formula: which comprises reacting a compound of the formula: with ethylene glycol to form a compound of the formula: reducing the nitro compound with a reducing agent to form an amine of the formula: reacting the amino compound with an alkylhaloformate to form a 2-carboalkoxyamino-5,6-methylene-dioxybenzaldehyde, reacting the 2-carboalkoxyamino compound with an anmonium salt in the present of an organic acid, and neutralizing the reaction mixture with a mild base.
Claim 23
Dependent Claim 12 words
The process of Claim 17 wherein the reducing agent is platinum dioxide.
Claim 24
Dependent Claim 15 words
or Claim 18 19. The process of Claim 17/wherein the ammonium salt is ammonium acetate.
Claim 25
Dependent Claim 20 words
or Claim 18 20. The process of Claim 17/wherein the acid is acetic acid and the base is ammonium hydroxide.
Claim 26
Dependent Claim 16 words
A compound according to any of Claims 1 to 7 for use as a therapeutic agent.

References Cited (Backward Citations)

DE2134451B2 Cited

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