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Last Updated: April 23, 2024

Claims for Patent: 4,321,254


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Summary for Patent: 4,321,254
Title: Antiallergic imidodisulfamides
Abstract:Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted tetrahydroisoquinoline and bis(chlorosulfonyl)imide in the presence of a tertiary amine. Pharmaceutical compositions and methods of inhibiting the symptoms of an allergic response are also disclosed.
Inventor(s): Ali; Fadia E. (Cherry Hill, NJ)
Assignee: SmithKline Corporation (Philadelphia, PA)
Application Number:06/191,644
Patent Claims:1. A compound of the formula (I) ##STR13## in which X is hydrogen, methyl, bromo or chloro; and Y is a phenylsulfonamido radical of the formula ##STR14## in which R is hydrogen or methyl; R.sub.1 is hydrogen, bromo, chloro, nitro, methyl, trifluoromethyl or methoxy; and R.sub.2 is hydrogen, chloro or methyl provided that when R.sub.2 is chloro, R.sub.1 is chloro, methyl or trifluoromethyl and when R.sub.2 is methyl R.sub.1 is methyl; or an alkali metal salt of said compound.

2. A compound according to claim 1 of the formula (II) ##STR15## in which X.sub.1 is hydrogen, methyl, bromo or chloro; R is hydrogen or methyl; R.sub.1 is hydrogen, bromo, chloro, nitro, methyl, trifluoromethyl or methoxy; and R.sub.2 is hydrogen, chloro or methyl provided that when R.sub.2 is chloro, R.sub.1 is chloro, methyl or trifluoromethyl and when R.sub.2 is methyl R.sub.1 is methyl; or an alkali metal salt of said compound.

3. A compound according to claim 2 in which X.sub.1 is hydrogen.

4. A compound according to claim 3 which is N,N'-bis[7-(4-chlorophenylsulfonamido-1,2,3,4-tetrahydroisoquinolyl]disulf onylamide or an alkali metal salt thereof.

5. A compound according to claim 1 of the formula (III) ##STR16## in which X.sub.2 is methyl, bromo or chloro; R is hydrogen or methyl; R.sub.1 is hydrogen, bromo, chloro, nitro, methyl, trifluoromethyl or methoxy; and R.sub.2 is hydrogen, chloro or methyl provided that when R.sub.2 is chloro, R.sub.1 is chloro, methyl or trifluoromethyl and when R.sub.2 is methyl, R.sub.1 is methyl or an alkali metal salt thereof.

6. A compound according to claim 1 of the formula (IV) ##STR17## in which X.sub.3 is hydrogen, methyl, bromo or chloro; R is hydrogen or methyl; R.sub.1 is hydrogen, bromo, chloro, nitro, methyl, trifluoromethyl or methoxy; and R.sub.2 is hydrogen, chloro or methyl provided that when R.sub.2 is chloro, R.sub.1 is chloro, methyl or trifluoromethyl and when R.sub.2 is methyl, R.sub.1 is methyl or an alkali metal salt thereof.

7. A compound according to claim 1 of the formula ##STR18## in which X.sub.4 is methyl, bromo or chloro; R is hydrogen or methyl; R.sub.1 is hydrogen, bromo, chloro, nitro, methyl, trifluoromethyl or methoxy; and R.sub.2 is hydrogen, chloro or methyl provided that when R.sub.2 is chloro, R.sub.1 is chloro, methyl or trifluoromethyl and when R.sub.2 is methyl, R.sub.1 is methyl or an alkali metal salt thereof.

8. A pharmaceutical composition for inhibiting the symptoms of asthma comprising a pharmaceutical carrier or diluent and an amount sufficient to produce said inhibition of a compound of claim 1.

9. A pharmaceutical composition according to claim 8 in a form suitable for administration by inhalation.

10. A pharmaceutical composition according to claim 8 comprising a solution or suspension of the active ingredient in sterile water.

11. A pharmaceutical composition according to claim 8 in the form of an aerosol formulation.

12. A pharmaceutical composition according to claim 8 in which the pharmaceutical carrier or diluent is a solid.

13. A method of inhibiting the symptoms of asthma which comprises administering to a subject in need of said inhibition a therapeutically effective amount for producing said inhibition of a compound of claim 1.

14. The method according to claim 13 in which the active ingredient is administered in a daily dosage regimen of from about 0.5 mg. to about 2000 mg.

15. A method of antagonizing the effects of SRS-A on bronchial smooth muscle which comprises administering to a subject in need of said antagonism an amount sufficient to produce said antagonism of a compound of claim 1.

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