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US 6,441,008 B1Granted
Benzamide derivatives as thrombin inhibitors
AssigneeSmithKline Beecham Corporation
InventorsHenry Anderson Kelly, Martin Pass, David Neil Smith
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Abstract
There are provided according to the invention novel compounds of formula (I) wherein R1 represents C1-4alkyl or C3-8cycloalkyl, R2 represents C1-4alkyl or C3-4alkenyl, R3 represents hydrogen, C1-3alkyl or halogen, and R4 represents C1-6alkyl, processes for preparing them, pharmaceutical formulations containing them and their use in therapy particularly as thrombin inhibitors.
Claims10
A compound of formula (I)
- wherein
- R1 represents C1-4alkyl or C3-8cycloalkyl;
- R2 represents C1-4alkyl or C3-4alkenyl;
- R3 represents hydrogen, C1-3alkyl or halogen;
- R4 represents C1-6alkyl;
- or a pharmaceutically acceptable derivative or solvate thereof.
3 more elements
A compound selected from:
- N-Ethyl-N-isopropyl-3-methyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N,N-Diisopropyl-3-methyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N-Isopropyl-3,N-dimethyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- 3,N-Dimethyl-N-propyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- 3-Methyl-N,N-dipropyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N-Ethyl-3-methyl-N-propyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N-Butyl-3-methyl-N-propyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N-Cyclohexyl-N-isopropyl-3-methyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- N-Isopropyl-3-methyl-N-propyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- 3-Chloro-N-isopropyl-N-propyl-5-[2S-(pyridin-4-ylamino)-propoxy]-benzamide;
- 3-Chloro-N,N-diisopropyl-5-[2-(pyridin-4-ylamino)-butoxy]-benzamide;
- or a pharmaceutically acceptable derivative or solvate thereof.
9 more elements
The compound:
- N-ethyl-N-isopropyl-3-methyl-5-[2S-(pyridin-4-ylamino)propoxy]benzamide 4-methylbenzenesulfonate, or a pharmaceutically acceptable derivative or solvate thereof.
A process for preparing a compound of formula (I):
- wherein
- R1 represents C1-4alkyl or C3-8cycloalkyl;
- R2 represents C1-4alkyl or C3-4alkenyl;
- R3 represents hydrogen, C1-3alkyl or halogen;
- R4 represents C1-6alkyl;
- or a pharmaceutically acceptable derivative or solvate thereof;
- which process comprises any one of:
- (A) deprotection of a compound of formula (II),
- where P1 represents a suitable protecting group;
- (B) reacting a compound of formula (III) with a compound of formula (IV)
- where R7 represents hydrogen, and L represents hydroxyl;
- (C) reacting a compound of formula (III) with a compound of formula (IV) where R7 represents hydrogen, and L represents a suitable leaving group, in the presence of a base;
- or
- (D) reacting a compound of formula (V) with a compound of formula (VI),
- where R7 represents hydrogen, in the presence of an activating agent or agents and a base.
12 more elements
Dependencies are inferred from the claim text.