2-amino-1,2,3,4-tetrahydronaphthalene derivatives with cardiovascular activity, process for their preparation and pharmaceutical compositions containing them

• US 5,096,929 A
• Filed: 06/26/1990
• Issued: 03/17/1992
• Est. Priority Date: 06/27/1989
• Status: Expired due to Fees

• Current Assignee: Chiesi Farmaceutici SPA (Valline Srl)
• Original Assignee: Chiesi Farmaceutici SPA (Valline Srl)
• Inventors: Delcanale, Maurizio, Chiesi, Paolo, Bongrani, Stefano, Servadio, Vittorino
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US07/544,201
• Time in Patent Office: 630 Days
• Field of Search: 564/364, 564/428, 514/653, 514/657
• US Class Current: 514/653
• CPC Class Codes: A61P 9/04 Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
• CPC Class Codes: A61P 9/08 Vasodilators for multiple indications
• CPC Class Codes: C07C 217/74 with rings other than six-membered aromatic rings being part of the carbon skeleton
• CPC Class Codes: C07C 2602/10 the other ring being six-membered, e.g. tetraline

Abstract

5,6-Dimethoxy-2-[2-(4-hydroxyphenyl)-2-hydroxy-2-methylethyl]amino- 1,2,3,4-tetrahydronaphthalene has inotropic and vasodilating activities and therefore can be used in the treatment of cardiocirculatory failure. The compound can be in the form of a single stereoisomer or as a mixture of two or more stereoisomers.

Claims

1. A compound selected from the group consisting of (i) a stereoisomer or mixture of stereoisomers of the formula:

##STR9## and (ii) the pharmaceutically acceptably salts of said stereoisomer or mixture of stereoisomers.

2. A compound according to claim 1 which is erythro5,6-dimethoxy2-[2-(4-hyroxyphenyl)-2-hyroxy-10methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 in which threo-5,6-dimethoxy-2-[2-(4-hyroxyphenyl)-2-hydroxy-1-methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 1 wherein the configuration about the carbon atom designated α

is R and the configuration about the carbon atom designated β

is S.

5. A compound according to claim 4 which is (-)(α

R, β

S, γ

S)-5,6-dimethoxy-2-( 4-hyroxyphenyl)-2-hydroxy-1methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

6. a compound according to claim 4 which is (+) (α

R, β

S, γ

R)-5,6-dimethoxy-2-[2-(4-hydroxyphenyl)-2-hydroxy-1methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

7. A compound according to claim 1 wherein the configuration about the carbon atom designated α

is S and the configuration about the carbon atom designated β

is R.

8. A compound according to claim 7 which is (+) (α

S, β

R, γ

R)-5,6-dimethoxy-2-[2-(4-hyroxyphenyl)-2-hyroxy-1-methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

9. A compound according to claim 7 which his (-) (α

S, β

R, γ

S)-5,6-dimethoxy-2-[2-(4-hyroxyphenyl)-2-hydroxy-1-methylethylamino]-1,2,3,4-tetrahydronaphthalene or a pharmaceutically acceptable salt thereof.

10. A pharmaceutical composition comprising a quantity of a compound according to claim 1 sufficient to effect stimulation of cardiac β

adrenergic receptors, and a pharmaceutical carrier.

11. The method of stimulation of cardiac β

adrenergic receptors in a human in need thereof which comprises administering thereto an effective amount of a compound according to claim 1.