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Details for Patent: 5,508,306

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Details for Patent: 5,508,306

Title: Aromatic amine derivatives
Abstract:This invention relates to novel aromatic amine compounds having the structure: ##STR1## where each W, Z.sup.1 and Z.sup.2 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, F, Cl, Br, I, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; where each R.sup.1 and R.sup.2 is independently H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; where each X and Y is independently CH.sub.2, NR.sup.4, S, S.dbd.O, SO.sub.2 ; where n is 0, 1 or 2; where each p and q is independently 1 or 2; where R.sup.3 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; where R.sup.4 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or COR.sup.3 ; and where R.sup.5 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl, C.sub.1 -C.sub.6 straight or branched chain alkoxy or OH. In addition the invention includes using such compounds for the treatment of benign prostatic hyperplasia, lowering intraocular pressure and inhibiting cholesterol synthesis.
Inventor(s): Chiu; George (Bridgewater, NJ), Gluchowski; Charles (Wayne, NJ)
Assignee: Synaptic Pharmaceutical Corporation (Paramus, NJ)
Filing Date:Sep 09, 1993
Application Number:08/124,501
Claims:1. A compound having the structure: ##STR139## wherein each W and Z.sup.1 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, F, Cl, Br, I, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; wherein Z.sup.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, F, Cl, Br, I, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; wherein each R.sup.1 and R.sup.2 is independently H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein X and Y are CH.sub.2 ; wherein n is 0, 1 or 2; wherein each p and q is independently 1 or 2; wherein R.sup.3 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein R.sup.4 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or COR.sup.3 ; and wherein R.sup.5 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl, C.sub.1 -C.sub.6 straight or branched chain alkoxy or OH.

2. A compound having the structure: ##STR140## wherein each W and Z.sup.1 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; Z.sup.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; wherein each R.sup.1 and R.sup.2 is independently H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein X and Y are CH.sub.2 ; wherein n is 0, 1 or 2; wherein each p and q is independently 1 or 2; wherein R.sup.3 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein R.sup.4 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or COR.sup.3 ; and wherein R.sup.5 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl, C.sub.1 -C.sub.6 straight or branched chain alkoxy or OH.

3. The compound of claim 1, wherein W is H.

4. The compound of claim 1, wherein n is 1.

5. The compound of claim 1, wherein R.sup.1 and R.sup.2 are both H.

6. The compound of claim 1, wherein p is 1.

7. The compound of claim 1, wherein q is 2.

8. The compound of claim 1, wherein p is 1 and q is 2.

9. The compound of claim 1, wherein Z.sup.2 is OCH.sub.3 and Z.sup.1 is H.

10. The compound of claim 1 having the structure: ##STR141##

11. The compound of claim 1 having the structure: ##STR142##

12. The compound of claim 1 having the structure: ##STR143##

13. A composition comprising a therapeutically effective amount of the compound of claim 1 or 2 and a pharmaceutically acceptable carrier.

14. A method for treating benign prostatic hyperplasia in a subject which comprises administering to the subject an amount of a compound having the structure: ##STR144## wherein each W, Z.sup.1 and Z.sup.2 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, OH, F, Cl, Br, I, NO.sub.2, CN, SO.sub.2 NHR.sup.3, NR.sup.4.sub.2, CONR.sup.3.sub.2, COR.sup.5 ; wherein each R.sup.1 and R.sup.2 is independently H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein each X and Y is independently CH.sub.2, NR.sup.4, C.dbd.O, S, S.dbd.O, SO.sub.2 ; wherein n is 0, 1 or 2; wherein each p and q is independently 1 or 2; wherein R.sup.3 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl; wherein R.sup.4 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or COR.sup.3 ; and wherein R.sup.5 is H, C.sub.1 -C.sub.6 straight or branched chain alkyl or phenyl, C.sub.1 -C.sub.6 straight or branched chain alkoxy or OH.

15. A method for treating benign prostatic hyperplasia in a subject which comprises administering to the subject an amount of a compound having the structure of claim 1.

16. A method for treating benign prostatic hyperplasia in a subject which comprises administering to the subject an amount of a compound having the structure of claim 2.
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