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4-amino-(ethylamino)-oxindole dopamine autoreceptor agonists

An alkyl and phenyl technology, applied in the field of 4-amino-oxindole, can solve the problems such as no disclosure or suggestion of receptor agonists

Inactive Publication Date: 2001-05-30
AMERICAN HOME PRODUCTS CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure or suggestion in this document that these compounds have D 2 Agonist activity may relieve symptoms of Parkinson's disease, schizophrenia, or other disorders affected by dopamine

Method used

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  • 4-amino-(ethylamino)-oxindole dopamine autoreceptor agonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] 4-(2-Benzylamino-ethylamino)-1,3-dihydro-indol-2-one Dihydrochloric acid

[0090] Salt 0.1 water

[0091] N-[2-(Benzyl-trifluoroacetylamino)ethyl]-2,2,2-trifluoro-N-(2-oxo-2,3-dihydro-1H-indole-4- Base)-acetamide (1.0 g, 2.1 mmol) was dissolved in 40 ml of tetrahydrofuran, and at room temperature, a solution formed by dissolving 50% sodium hydroxide (1.0 ml) in 10 ml of methanol was added. After 15 minutes, the mixture was concentrated and the residue was dissolved in 50 mL of ethyl acetate. The organic layer was washed with 2 x 50ml of water, 50ml of brine, dried over anhydrous magnesium sulfate, and filtered. Purification by silica gel chromatography (7% 2N ammonia methanol-ethyl acetate), crystallization from ethyl acetate gave the free base as a light green solid (0.7 g, 87.5%), mp 120-124°C; MS EI m / e 281 ( m + ).

[0092] C 17 h 19 N 3 O 0.25H 2 Elemental analysis of O

[0093] Calculated: C, 71.43; H, 6.88; N, 14.70

[0094] Found va...

Embodiment 2

[0100] 4-[2-(Benzyl-methyl-amino)-ethylamino]-1,3-dihydro-indol-2-one·di

[0101] Hydrochloride·0.8 water

[0102] N-[2-(Benzyl-methyl-amino)ethyl]-N-(3-chloro-1H-indol-4-yl)-2,2,2-trifluoroacetamide (5b, 1.75 g , 4.27mmol) was dissolved in 27ml of acetic acid to form a solution, and 70% phosphoric acid (20ml) was added. The reaction was heated at 75-80°C for 16 hours. The mixture was poured into 100ml of water and the crude product crystallized out as a solid. After filtration, the solid was dissolved in 100 ml of ethyl acetate*, washed with 50 ml of water, 50 ml of saturated sodium bicarbonate solution and 20 ml of brine, dried over anhydrous magnesium sulfate, and filtered. Concentration with ethyl acetate gave crude intermediate 6b as a dark green residue (1.5 g). Without further purification, this material was dissolved in 40 ml of tetrahydrofuran, and a mixture of 1.0 ml of 50% sodium hydroxide dissolved in 10 ml of methanol was added at room temperat...

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PUM

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Abstract

Compounds having dopaminegic activity are provided or pharmaceutically acceptable salts thereof, having formula (I) wherein R<1> and R<2> are each, independently, hydrogen, C1-10 alkyl, or (CH2)mR<4>, wherein R<4> is phenyl or naphthyl which may be substituted by one or two substituents selected from the group consisting of C1-6 alkyl, halogen, C1-6 alkoxide and trifluoromethyl and m is 1 to 5; and R<3> is hydrogen or C1-6 alkyl.

Description

field of invention [0001] The present invention relates to a series of 4-amino-(ethylamino)-oxindoles having dopaminergic properties. The compounds of this invention are useful in the treatment of various diseases affected by dopamine agonists, such as Parkinson's disease, Tourette's syndrome, schizophrenia and alcohol and drug addiction. Background of the invention [0002] Efforts to induce antipsychotic activity with dopamine autoreceptor agonists have been successful (see, for example, Dorsini et al., Adv. Biochem. Psychopharmacol., 16:645-648 (1977); Tamminga et al., Science. 200:567 -568 (1975); and Tamminga et al., Psychiatry 398-402 (1986)). Recently Lahti et al, in Mol.Pharm., 42: 432-438 (1993) reported a dopamine D 2 Methods for Assaying Intrinsic Activity on Receptors. The ratio of the low affinity agonist state (ie, LowAg) to the high affinity agonist state (ie, HighAg) of the receptor, ie, LowAg / HighAg, is used to predict intrinsic activity. These ratios re...

Claims

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Application Information

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IPC IPC(8): A61K31/404A61K31/403A61P25/00A61P25/16A61P25/18A61P25/30A61P43/00C07D209/34
CPCC07D209/34A61P25/00A61P25/16A61P25/18A61P25/30A61P43/00
Inventor J·A·内尔森M·A·坎泽贝格尔R·E·穆肖
Owner AMERICAN HOME PRODUCTS CORPORATION
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