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Dihydropyridine compounds, their production, and pharmaceutical compositions containing them

Assignee: Astellas Pharma Inc
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Filing: 1985-06-28
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Granted: —
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Expires: 2005-06-28
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Abstract

Abstract The invention provides a dihydropyridine compound of the following general formular (I) or a salt thereof: wherein R' and R 2 are the same or different and selected from C, to C 10 alkyl groups, C, to C 5 alkyl groups interrupted by oxygen atom(s), and C, to C 5 alkyl groups substituted by C 3 to C 6 alicyclic group(s); R 3 and R 4 are the same or different C, to C 5 alkyl groups; R 5 and R 6 are the same or different and selected from hydrogen and halogen atoms and nitro, C, to C 5 alkyl, C, to C 5 alkoxy, C, to C 5 alkylthio, C, to C 5 alkylsulfonyl and C, to C 5 alkylsulfinyl groups; R 7 and R 8 are the same or different and are selected from hydrogen and halogen atoms and cyano, C, to C 5 alkoxy and C, to C 5 alkanoylamino groups or combine to form, with the adjacent phenyl group, a naphthyl group; A represents a single bond, or a vinylene (-CH=CH-) or ethynylene group (-C≡C-); B represents a single bond or -CH 2 0-; and m and n are the same or different and selected from 0 and integers of 1 to 5, and methods of making such a compound. The compounds may be used for treatment or prevention of ischemic heart-disease and cardiovascular disorders and may show both Ca 2+ -antagonistic action and adrenergic betareceptor

Inventors

  • 👤 Takashi Fujikura
  • 👤 Noriki Ito
  • 👤 Yuzo Matsumoto
  • 👤 Yasuo Isomura
  • 👤 Masaharu Asano
  • 👤 Toichi Takenaka

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-28 15:10
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/82; C07D401/00; C07D401/02; C07D401/12; A; A61; A61P; A61P25/00; A61P25/02; A61P25/28; A61P9/00; A61P9/06; A61P9/08; A61P9/10; A61P9/12; C07C; C07C317/00; C07C323/00; C07D211/84; C07D211/90

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 214 words
A dihydropyridine compound of the following general formula (I) or a salt thereof: wherein R 1 and R 2 are the same or different and selected from C 1 to C 10 alkyl groups, C 1 to C 5 alkyl groups interrupted by oxygen atom(s), and C 1 to C 5 alkyl groups substituted by C 3 to C 6 alicyclic group(s); R 3 and R are the same or different C 1 to C 5 alkyl groups; R 5 and R 6 are the same or different and selected from hydrogen and halogen atoms and nitro, C 1 to C 5 alkyl,C 1 to C 5 alkoxy, C 1 to C 5 alkylthio, C 1 to C 5 alkylsulfonyl and C 1 to C 5 alkylsulfinyl groups; R 7 and R 8 are the same or different and are selected from hydrogen and halogen atoms and cyano, C 1 to C 5 alkoxy and C 1 to C 5 alkanoylamino groups or combine to form,with the adjacent phenyl group, a naphthyl group; A represents a single bond, or a vinylene (-CH=CH-) or ethynylene group (-C≡C-); B represents a single bond or -CH 2 0-; and m and n are the same or different and selected from 0 and integers of 1 to 5.
Claim 2
Dependent Claim 214 words
A dihydropyridine compound of the following general formula (I) or a salt thereof: wherein R 1 and R 2 are the same or different and selected from C 1 to C 10 alkyl groups, C 1 to C 5 alkyl groups interrupted by oxygen atom(s), and C 1 to C 5 alkyl groups substituted by C 3 to C 6 alicyclic group(s); R 3 and R are the same or different C 1 to C 5 alkyl groups; R 5 and R 6 are the same or different and selected from hydrogen and halogen atoms and nitro, C 1 to C 5 alkyl,C 1 to C 5 alkoxy, C 1 to C 5 alkylthio, C 1 to C 5 alkylsulfonyl and C 1 to C 5 alkylsulfinyl groups; R 7 and R 8 are the same or different and are selected from hydrogen and halogen atoms and cyano, C 1 to C 5 alkoxy and C 1 to C 5 alkanoylamino groups or combine to form,with the adjacent phenyl group, a naphthyl group; A represents a single bond, or a vinylene (-CH=CH-) or ethynylene group (-C≡C-); B represents a single bond or -CH 2 0-; and m and n are the same or different and selected from 0 and integers of 1 to 5.
Claim 3
Dependent Claim 37 words
A compound according to claim 1 wherein R 1 and R 2 are the same or different C 1 to C 5 alkyl groups, R 7 is a hydrogen atom, and R 8 is a hydrogen atom.
Claim 4
Dependent Claim 33 words
A compound according to claim 2 wherein R 5 and R 6 are the same or different and selected from a hydrogen atom and a nitro group, and B is -CH 2 0-.
Claim 5
Dependent Claim 23 words
At least one compound according to claim 1 selected from dimethyl 4-[ 2-[ 4-(2-hydroxy-3-phenoxypropylamino)butoxy ]-5-nitrophenyl]-2,6-dimethyL-1, 4-dihydropyridine-3,5-dicarboxylate, (S)-(-)-dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, R(+)-dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypronylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, and salts thereof.
Claim 6
Dependent Claim 229 words
A process for producing a compound of the formula (I) which comprises reacting a compound of the formula (II) with a compound of the formula (III) wherein R 1 and R 2 are the same or different and selected from C 1 to C 10 alkyl groups, C 1 to C 5 alkyl groups interrupted by oxygen atom(s), and C to C 5 alkyl groups substituted by C 3 to C 6 alicyclic group(s); R 3 and R 4 are the same or different C 5 to C 5 alkyl groups; R 5 and R 6 are the same or different and selected from hydrogen and halogen atoms and nitro, C 1 to C 5 alkyl, C 1 to C 5 alkoxy, C 1 to C 5 alkylthio, C 1 to C 5 alkylsulfonyl and C 1 to C 5 alkylsulfinyl groups; R 7 and R 8 are the same or different and are selected from hydrogen and halogen atoms and cyano, C 1 to C 5 alkoxy ana C 1 to C 5 alkanoylamino groups or combine to form, with the adjacent phenyl group, a naphthyl group; A represents a single bond, or a vinylene (-CH=CH-) or ethynylene group (-C≡C-); B represents a single bond or -CH 2 O-; and m and n are the same or different and selected from 0 and integers of 1 to 5.
Claim 7
Dependent Claim 229 words
A process for producing a compound of the formula (I) which comprises reacting a compound of the formula (II) with a compound of the formula (III) wherein R 1 and R 2 are the same or different and selected from C 1 to C 10 alkyl groups, C 1 to C 5 alkyl groups interrupted by oxygen atom(s), and C to C 5 alkyl groups substituted by C 3 to C 6 alicyclic group(s); R 3 and R 4 are the same or different C 5 to C 5 alkyl groups; R 5 and R 6 are the same or different and selected from hydrogen and halogen atoms and nitro, C 1 to C 5 alkyl, C 1 to C 5 alkoxy, C 1 to C 5 alkylthio, C 1 to C 5 alkylsulfonyl and C 1 to C 5 alkylsulfinyl groups; R 7 and R 8 are the same or different and are selected from hydrogen and halogen atoms and cyano, C 1 to C 5 alkoxy ana C 1 to C 5 alkanoylamino groups or combine to form, with the adjacent phenyl group, a naphthyl group; A represents a single bond, or a vinylene (-CH=CH-) or ethynylene group (-C≡C-); B represents a single bond or -CH 2 O-; and m and n are the same or different and selected from 0 and integers of 1 to 5.
Claim 8
Dependent Claim 52 words
A process for producing a compound of the formula (I) as defined in claim 5 which comprises reacting a compound of the formula(IV) with a compound of the formula (V) wherein X represents a halogen atom or an organic sulfonic acid radical and the other substituents are as defined in claim 5.
Claim 9
Dependent Claim 69 words
A process for producing a compound of the formula (I) as defined in claim 5 which comprises reacting a compound of the formula (VI) with a compound of the formula .(V) to give a Schiff base (VII) and then reducing the Schiff base without reducing any nitro group(s), wherein n' represents O or an integer of 1 to 4 and the other substituents are as defined in claim 5.
Claim 10
Dependent Claim 40 words
A process for producing a compound of the formula (I) as defined in claim 5 which comprises reacting a compound of the formula (II) with a compound of the formula (VIII) wherein the substituents are as defined in claim 5.
Claim 11
Dependent Claim 11 words
A pharmaceutical composition containing a compound according to any preceding claim.
Claim 12
Dependent Claim 45 words
The use of a compound according to any preceding claim for the manufacture of a medicament (a) which shows both Ca 2+ -antagonistic action and adrenergic beta- receptor blocking activity and/or (b) which is for the treatment or prevention of ischemic heart-disease and cardiovascular disorders.

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