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Details for Patent: 4,373,106

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Details for Patent: 4,373,106

Title: Sulfamoyl-substituted phenethylamine derivatives and process of producing them
Abstract:Novel sulfamoyl-substituted phenethylamine derivatives which exhibit .alpha.-adrenergic blocking action and are useful as an antihypertensive agent and an agent for the treatment of congestive heart failure.
Inventor(s): Imai; Kazuo (Omiya, JP), Niigata; Kunihiro (Ageo, JP), Fujikura; Takashi (Urawa, JP), Hashimoto; Shinichi (Matsudo, JP), Takenaka; Toichi (Tokyo, JP)
Assignee: Yamanouchi Pharmaceutical Co., Ltd. (Tokyo, JP)
Filing Date:Feb 04, 1981
Application Number:06/231,421
Claims:1. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR89## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group, or a lower alkoxy group; R.sub.3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a phenylthio group, or a phenylsulfinyl group; R.sub.4, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group and Y represents an oxygen atom or a methylene group; said Y is an oxygen atom when R.sub.2 is a hydroxyl group or the salts thereof which comprises condensing a compound represented by the formula ##STR90## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same significance as in the above formula

and a compound represented by the formula ##STR91## wherein R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula

and then reducing the condensation product.

2. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR92## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents a chlorine or bromine atom; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; said Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR93## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a chlorinating or brominating agent.

3. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR94## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxy group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents a hydrogen atom or a lower alkyl group; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; said Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR95## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a halogenating agent and reducing the halogenated product.

4. The process as defined in claim 3 for the preparation of 5-[2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl]-2-methoxybenzenesulfon amide.

5. The process as defined in claim 3 for the preparation of 2-methoxy-5-[2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl]-benzensulfo namide.

6. The process as defined in claim 3 for the preparation of 5-[2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl]-2-methylbenzenesulfon amide.

7. The process as defined in claim 3 for the preparation of 5-[2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide.

8. The process as defined in claim 3 for the preparation of 2-methoxy-5-[2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl]-N-methylben zenesulfonamide.

9. The process as defined in claim 3 for the preparation of 2-methoxy-5-[2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl]-N,N-dimethy lbenzenesulfonamide.

10. The process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR96## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents phenylsulfinyl; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; said Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR97## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a halogenating agent to form a halogenated product, reacting said halogenated product with an alkaline material, reacting the product thus obtained with thiophenol, and oxidizing the resulting product.

11. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR98## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents iodine; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; said Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR99## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a halogenating agent to form a halogenated product ##STR100## wherein X represents a chlorine atom or bromine atom and R and R.sub.6 are hydrogen, reacting said halogenated product with an alkaline material and then reacting the product ##STR101## thus obtained with hydrogen iodide.

12. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR102## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents a lower alkoxy group; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; and Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR103## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a halogenating agent fo form a halogenated product ##STR104## wherein X represents a chlorine atom or bromine atom and R and R.sub.6 are hydrogen, reacting said halogenated product with an alkaline material and then reacting the product ##STR105## thus obtained with a lower alcohol.

13. A process for producing sulfamoyl-substituted phenethylamine derivatives represented by the formula ##STR106## wherein R.sub.1 represents an amino group or a mono- or di-lower alkylamino group; R.sub.2 represents a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sub.3 represents phenylthio; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 each represent a hydrogen atom or a lower alkyl group; R.sub.10 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and Y represents an oxygen atom or a methylene group; said Y being an oxygen atom when R.sub.2 is a hydroxyl group, or the salts thereof which comprises reacting a compound represented by the formula ##STR107## wherein R represents a hydrogen atom or a lower alkyl group and R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and Y have the same significance as in the above formula with a halogenating agent to form a halogenated product ##STR108## wherein X represents a chlorine atom or bromine atom and R and R.sub.6 are hydrogen, reacting said halogenated product with an alkaline material and then reacting the product ##STR109## thus obtained with thiophenol.
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