# US 5,352,684 A · Pyridines as medicaments

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- Number: US 5,352,684 A
- Document ID: US5352684A
- Status: Granted
- Kind: A
- Application number: 07/934,738
- Filed: 1992-10-09
- Granted: 1994-10-04
- Earliest claimed: 1990-04-10
- Assignees: Byk Gulden Lomberg Chemische Fabrik GmbH
- Inventors: Peter Zimmermann; Wolf-Rudiger Ulrich
- Web page: https://patentgrep.com/patent/US5352684A

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Dihydropyridines of formula (I), in which the substituents and symbols have the meanings given in the description, are novel substances with interesting pharmacological properties. A method for their preparation and their uses are also presented.

## Claims

### Claim 1

A pyridine compound of formula I ##STR76## wherein one of the radicals R1 and R5 denotes 1-6C-alkyl and the other denotes the grouping -E1-E2-N(R6a)R6b
R2 denotes hydrogen, 1-6C-alkyl or, together with R3, 2-3C-alkylene,
R3 denotes 1-4C-alkyl, 1-4C-alkoxy, 3-5C-alkoxyalkyl, 3-5C-alkoxyalkoxy or, together with R2, 2-3C-alkylene,
R4 denotes phenyl which is substituted by R41 and R42,
R41 denotes hydrogen, hydroxyl, halogen, nitro, cyano, trifluoromethyl, 1-4C -alkyl, 1-4C-alkoxy, 1-4C-alkoxy which is completely or partly substituted by fluorine, 1-4C-alkoxycarbonyl, 2-5C-acyl, amino or mono- or di-1-4--C-alkylamino,
R42 denotes hydrogen, hydroxyl, halogen, nitro, cyano, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy which is completely or partly substituted by fluorine, 1-4C-alkoxycarbonyl, 2-5C-acyl; amino or mono-or di-1-4C-alkylamino,
E1 denotes methylene (CH.sub.2),
E2 denotes straight-chain or branched 1-7C-alkylene, the grouping -(CH.sub.2).sub.m -E-(CH.sub.2).sub.n -or the grouping -A1-O-A2-,
E denotes vinylene (--CH.dbd.CH--) or ethinylene (--C.dbd.C-),
m denotes the number 1 or 2,
n denotes the number 1 or 2,
A1 denotes a bond or 2-4C-alkylene,
A2 denotes 2-4C-alkylene or 2C-alkylenoxy-2C-alkylene,
R6a l and R6b, together and including the nitrogen atom to which they are both bonded, represent a radical of the formula ##STR77## wherein A denotes --CH.sub.2 --CH.sub.2 C(R7)R8--CH.sub.2 --CH.sub.2 -, --CH.sub.2 --CH.sub.2 CHR9--CH.sub.2 --CH.sub.2 - or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CHR10-,
R7 denotes hydrogen (H) or aryl and
R8 denotes aryl,
or
R7 and R8 together denote diarylmethylene,
R9 denotes diaryl-1-4C-alkyl and
R10 denotes aryl-1-4C-alkyl,
wherein
aryl represent a ring of the formula ##STR78## wherein R11 and R12 are identical or different and denote hydrogen (H), 1-4C-alkyl, 1-4C-alkoxy, halogen, hydroxyl, trifluoromethyl or, together, methylenedioxy, or salt thereof.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1, wherein
E2 denotes straight-chain or branched 1-5C-alkylene, the grouping -(CH.sub.2 .sub.m -E-(CH.sub.2).sub.n - or the grouping -Al-O-A2- and
A1 denotes 2-4C-alkylene, or a salt thereof.

### Claim 3 (depends on 1)

A compound of claim 1 of formula Ia ##STR79## wherein R1 denotes 1-6C-alkyl and R2, R3, R4, E1, E2, R6a and R6b have the meanings given in claim 1, or a salt thereof.

### Claim 4 (depends on 1)

A compound of claim 1 of formula Ib ##STR80## wherein R1 denotes 1-6C-alkyl and R2, R3, R4, E1, E2, R6a and R6b have the meanings given in claim 1, or a salt thereof.

### Claim 5 (depends on 1)

A compound of formula I according to claim 1, in which one of the radicals R1 and R5 denotes 1-6C-alkyl and the other denotes the grouping -E1-E2-n(R6a)R6b,
R2 denotes 1-4C-alkyl or, together with R3, 2-3C-alkylene,
R3 denotes 12-4C-alkyl, branched-chain 3-4C-alkoxy or, together with R2, 2-3C-alkylene,
R4 denotes phenyl which is substituted by R41 and R42,
R41 denotes hydrogen, chlorine or nitro,
R42 hydrogen or chlorine,
E1 denotes methylene (CH.sub.2),
E2 denotes ethylene, propylene, tetramethylene, pentamethylene, hexamethylene or the grouping -A1l-O-A2-,
A1 denotes a bond,
A2 denotes ethylene,
R6a and R6b, together and including the nitrogen atom to which they are both bonded, represent a radical of the formula ##STR81## wherein A denotes --CH.sub.2 --CH.sub.2 --C(R7(R8--CH.sub.2 --CH.sub.2 -, --CH.sub.2 --CH.sub.2 --CHR9--CH.sub.2 --CH.sub.2 - or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CHR10,
R7 denotes hydrogen or phenyl and
R8 denotes phenyl, or
R7 and R8 together denote diphenylmethylene,
R9 denotes diphenylmethylene (benzhydryl) and
R10 denotes benzyl or 4-chlorobenzyl, or a salt thereof.

### Claim 6 (depends on 1)

A compound of formula I according to claim 1, in which one of the radicals R1 and R5 denotes 1-4C-alkyl and the other denotes the grouping -E1-E2-N(R6a)R6b,
R2 denotes 1-4C-alkyl or, together with R3, 2-3C-alkylene,
R3 denotes 1-4C-alkyl, branched-chain 3-4C-alkoxy or, together with R2, 2-3C-alkylene,
R4 denotes 3-nitrophenyl or 2,3-dichlorophenyl,
E1 denotes methylene,
E2 denotes propylene, tetramethylene, pentamethylene, hexamethylene or the grouping -A1-O-A2,
A1 denotes a bond,
A2 denotes ethylene,
R6a and R6b, together and including the nitrogen atom to which they are both bonded, represent a radical of the formula ##STR82## wherein A denotes --CH.sub.2 --CH.sub.2 --C(R7(R8--CH.sub.2 --CH.sub.2 -,
R7 denotes phenyl an
R8 denotes phenyl, or
R7 and R8 together denote diphenylmethylene, or a salt thereof.

### Claim 7 (depends on 1)

A compound of formula I according to claim 1, in which one of the radicals R1 and R5 denotes 1-4C-alkyl and the other denotes the grouping -E1-E2-N(R6a)R6b,
R2 denotes 1-4C-alkyl,
R3 denotes 1-4C-alkyl or branched chain 3-4C-alkoxy,
R4 denotes 3-nitrophenyl,
R1 denotes methylene,
E2 denotes ethylene or propylene, R6a and R6b, together and including the nitrogen atom to which they are both bonded, represent a radical of the formula ##STR83## wherein A denotes --CH.sub.2 --CH.sub.2 --C(R7)R8--CH.sub.2 --CH.sub.2 -,
R7 denotes phenyl and
R8 denotes phenyl, or a salt thereof.

### Claim 8 (depends on 1)

A medicament composition containing a suitable carrier and an effective amount of one or more compounds according to claim 1, or a pharmacologically tolerated salt thereof.