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US 2003/0144525 A1Published application
Conjugated aromatic compounds with a pyridine substituent
AssigneeHoffmann-La Roche Inc.
InventorsAlexander Alanine, Bernd Buettelmann, Marie-Paule Heitz Neidhart, Emmanuel Pinard, Rene Wyler
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of formulae 1 The compounds of the present invention are NMDA (N-methyl-D-aspartate)-receptor subtype blockers and are used in the treatment of diseases related to this receptor.
Claims22
A compound of formulae
- 21
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl lower alkoxy, halogen, trifluoromethyl and hydroxy;
- Ar is selected from the group phenyl and thiophenyl;
- The dotted line is selected from the group two hydrogens not forming a bridge, and —CH2—CHR′—, wherein R′ is selected from the group lower alkyl and hydrogen;
- and
- is 0, 1 or 2;
- or a pharmaceutically acceptable acid addition salt thereof, with the proviso that when Ar is unsubstituted phenyl and R2 is H, R1 is not 2-amino:
7 more elements
A compound of formula
- 22
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group of hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy
- or a pharmaceutically acceptable acid addition salt thereof.
4 more elements
A compound of formula
- 23
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- and
- R′ is selected from the group lower alkyl and hydrogen;
- or a pharmaceutically acceptable acid addition salt thereof
5 more elements
A compound of formula
- 24
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- R′ is selected from the group lower alkyl and hydrogen;
- and
- n is 0, 1 or 2;
- or a pharmaceutically acceptable acid addition salt thereof.
7 more elements
A compound of formula
- 25
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- or a pharmaceutically acceptable acid addition salt thereof.
4 more elements
A process for preparing a compound of formula IA-1a comprising
- a) reacting a compound of formula
- 26
- with diphenyl phosphoryl azide, forming a compound of formula
- 27
- wherein
- R2 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- Ar is selected from the group phenyl and thiophenyl and
- n is 0, 1 or 2.
8 more elements
A process for preparing a compound of formula IA-1b comprising
- reacting the amino group of a compound of formula
- 28
- with a compound of formula R5X,
- forming a compound of formula
- 29
- wherein
- R2 is selected from the group hydrogen, lower alkyl,
- —(CH2)2NR5R5′ and —(CH2)n+1OH;
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl) lower alkoxy, halogen, trifluoromethyl and hydroxy;
- Ar is selected from the group phenyl and thiophenyl;
- R5 is lower alkyl;
- X is halogen;
- and;
- n is 0, 1 or 2.
11 more elements
A process for preparing a compound of formulae IIB-1a, comprising:
- reacting a compound of formula
- 30
- with diphenyl phosphoryl azide forming a compound of formula
- 31
- wherein
- R2 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- Ar is selected from the group phenyl and thiophenyl;
- R5 is lower alkyl;
- and;
- n is 0, 1 or 2.
8 more elements
A process for preparing a compound of formula IIB-1b comprising:
- reacting the amino group of a compound of formula
- 32
- with a compound of formula R5X
- forming a compound of formula
- 33
- wherein
- R1 is selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- R3 and R4 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- Ar is selected from the group phenyl and thiophenyl;
- X is halogen;
- and
- n is 0, 1 or 2.
10 more elements
A process for preparing a compound of formulae IA-2 comprising:
- reacting a compound of formula
- 34
- with a compound of formula
- 35
- forming a compound of formula
- 36
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- and
- is 0, 1 or 2.
10 more elements
A process for preparing a compound of formula IB-2 comprising:
- reacting a compound of formula
- 37
- with a compound of formula
- 38
- forming a compound of formula
- 39
- wherein
- R1 and R2 are each independently selected from the group hydrogen, lower alkyl, —(CH2)nNR5R5′ and —(CH2)n+1OH;
- R5 and R5′ are each independently hydrogen or lower alkyl;
- and
- R3 and R4 are each independently selected from the group hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl and hydroxy;
- and
- n is 0, 1 or 2.
10 more elements
Dependencies are inferred from the claim text.