Claims
- 1. A compound of Formula 1.0: ##STR27## and the pharmaceutically acceptable salts and solvates thereof wherein: (B) R.sup.3 is selected from the group consisting of:
- (1) alkyl;
- (2) --CH.sub.2 -phenyl;
- (3) phenyl:
- (4) substituted phenyl;
- (7) 3-(2-chloro-4-methoxyphenoxypropyloxymethyl;
- (8) --(CH.sub.2).sub.a R.sup.11 wherein a is an integer of 1 to 6 and R.sup.11 is selected from the group consisting of --C(O)OR.sup.12, --OR.sup.12, R.sup.12, and --N(R.sup.12).sub.2, wherein each R.sup.12 can be the same or different and is selected from the group consisting of alkyl, alkenyl and H; and
- (9) --OR.sup.13 wherein R.sup.13 is selected from the group consisting of H, alkyl- which may be substituted with OH, SH, NH.sub.2 and/or halogen -, alkenyl;
- (C) R.sup.1 is
- (1) H;
- (2) alkyl;
- (5) alkenyl;
- (D) Each R.sup.2 for each m is independently selected from the group consisting of:
- (1) alkyl;
- (2) alkoxy;
- (3) phenoxy;
- (4) phenyl
- (5) --O--CH.sub.2 -phenyl;
- (6) halogen atoms selected from the group consisting of F, Cl, Br and I;
- (7) --O--CO--R.sup.6 wherein R.sup.6 is alkyl- which may be substituted with OH, SH, NH.sub.2 and/or halogen -; phenyl; and alkenyl;
- (8) --N(R.sup.7).sub.2 wherein each R.sup.7 is independently selected from the group consisting of H, alkyl, phenyl, and R.sup.6 C(O)-- wherein R.sup.6 is as above defined;
- (9) --OH;
- (10) --CH.sub.2 OH;
- (11) --COOH;
- (12) --COOR.sup.8, wherein R.sup.8 is selected from the group consisting of alkyl and phenyl;
- (13) --SO.sub.3 H;
- (14) --SO.sub.2 NHR.sup.9, wherein R.sup.9 is selected from the group consisting of alkyl, phenyl, and H;
- (15) --PO.sub.3 H;
- (16) --PO(OR.sup.10).sub.2, wherein R.sup.10 is selected from the group consisting of alkyl and phenyl;
- (17) --OPO.sub.3 H;
- (18) --OP(OR.sup.10).sub.2 wherein R.sup.10 is as above defined; and
- (19) --CF.sub.3 ;
- (E) m is an integer from 0 to 1; and
- (F) R.sup.4 is selected from the group consisting of H, aminoalkyl and hydroxyalkyl
- and wherein
- acyl represents alkyl-C(O)-, alkenyl-C(O)-, alkynyl-C(O)-, cycloalkyl-C(O)-, phenyl-C(O)- or cycloalkenyl-C(O)-;
- alkaryl represents an phenyl group, as defined below, in which an alkyl group, as defined below, is substituted for one of the phenyl H atoms;
- alkenyl represents straight and branched aliphatic hydrocarbon groups having 1 bond and having from 2 to 6 carbon atoms;
- alkoxy represents an alkyl radical attached to a molecule through an oxygen atom (-O-alkyl);
- alkyl represents straight or branched saturated hydrocarbon groups which have from 1 to 6 carbon atoms;
- aminoalkyl represents NH.sub.2 -alkyl, alkyl-NH.sub.2 -alkyl, (alkyl).sub.2 NH.sub.2 -alkyl;
- cycloalkenyl represents a carbocyclic ring having from 5 to 7 carbon atoms and one carbon-to-carbon double bond in the ring;
- cycloalkyl represents a saturated carbocyclic ring having from 3 to 7 carbon atoms;
- hydroxyalkyl represents an alkyl group wherein one or two hydroxy groups is substituted for one or two hydrogen atoms; and
- substituted alkyl represents an alkyl group, as defined above, wherein one of the alkyl H atoms is replaced with a group selected from the group consisting of alkyl, aryl, heteroaryl,--OH, --O-alkyl, --NH.sub.2, --N(alkyl).sub.2 wherein each alkyl group is the same or different, --SH, --S-alkyl, --C(O)O-alkyl, --C(O)H, --NHC(:NH)NH.sub.2, --C(O)NH.sub.2, --OC(O)NH.sub.2, NO.sub.2 and --NHC(O)-alkyl, wherein alkyl, aryl, and heteroaryl are as above defined.
- 2. A compound of claim 1 wherein R.sup.2 is selected from the group consisting of:
- (1) --CH.sub.3 ;
- (2) --OCH.sub.3 ;
- (3) --OCOCH.sub.3 ;
- (4) --OCH.sub.2 -phenyl;
- (5) Cl;
- (6) F;
- (7) I; and
- (8) --CF.sub.3.
- 3. A compound of claim 1 wherein R.sup.3 is selected from the group consisting of:
- (1) --CH.sub.3 ;
- (2) --C.sub.6 H.sub.13 ;
- (3) --C.sub.7 H.sub.15,
- (4) --CH.sub.2 -phenyl;
- (6) phenyl; ##STR28## (8) --CH.sub.2 CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 ; and (9) --CH.sub.2 CO.sub.2 CH.sub.3.
- 4. A compound of claim 3 wherein:
- (A) X is NR.sup.3 ;
- (C) R.sup.2 is selected from the group consisting of:
- (1) --CH.sub.3 ;
- (2) --OCH.sub.3 ;
- (3) --OCOCH.sub.3 ;
- (4) --OCH.sub.2 -phenyl;
- (5) Cl;
- (6) F;
- (7) I; and
- (8) --CF.sub.3 ; and m is 0, 1 or 2;
- (D) R.sup.3 is selected from the group consisting of:
- (1) --CH.sub.3 ;
- (2) --C.sub.6 H.sub.13 ;
- (3) --C.sub.7 H.sub.15 ;
- (4) --CH.sub.2 -phenyl;
- (6) phenyl; ##STR29## (8) --CH.sub.2 CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 ; and (9) --CH.sub.2 CO.sub.2 CH.sub.3 ; and R.sup.4 is --O(CH.sub.2).sub.2 N(CH.sub.3).sub.2.
- 5. The compound of claim 1 wherein R.sup.4 is an aminoalkyl group.
- 6. The compound of claim 5 wherein R.sup.4 is --(CH.sub.2).sub.2 N(CH.sub.3).sub.2.
- 7. The compound of claim 6 R.sup.2 is alkyl.
- 8. The compound of claim 7 wherein R.sup.2 is --CH.sub.3.
- 9. A compound selected from the group consisting of ##STR30##
- 10. A compound selected from the group consisting of ##STR31##
- 11. The compound of claim 1 wherein:
- (B) R.sup.1 is selected from the group consisting of H and alkyl;
- (C) R.sup.2 is --CH.sub.3 and m is 0 or 1;
- (D) R.sup.3 is selected from the group consisting of:
- (1) --C.sub.6 H.sub.13 ;
- (2) --C.sub.7 H.sub.15 ; and
- (3) --CH.sub.2 -phenyl; and
- (E) R.sup.4 is --O(CH.sub.2).sub.2 N(CH.sub.3).sub.2.
- 12. The maleate salt of a compound of claim 1 wherein R.sup.4 is --O(CH.sub.2).sub.2 N(CH.sub.3).sub.2.
- 13. A pharmaceutical composition comprising an effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 14. A method of treating hypertension in a patient in need of such treatment comprising administering to such patient an effective antihypertensive amount of a compound of claim 5.
Parent Case Info
The present application is the U.S. national application corresponding to International Application No. PCT/US 91/06250, filed Sep. 6, 1991 and designating the United States, which PCT application is in turn a continuation-in-part of U.S. application Ser. No. 07/579,749, filed Sep. 7, 1990, the benefit of which applications are claimed pursuant to the provisions of 35 U.S.C. .sctn..sctn.120, 363 and 365(C).
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US91/06250 |
9/6/1991 |
|
|
3/1/1993 |
3/1/1993 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO92/04328 |
3/19/1992 |
|
|
US Referenced Citations (13)
Foreign Referenced Citations (5)
Number |
Date |
Country |
59698 |
Sep 1982 |
EPX |
172004 |
Feb 1986 |
EPX |
44-16373 |
Jul 1969 |
JPX |
1207771 |
Oct 1990 |
GBX |
9204328 |
Mar 1992 |
WOX |
Non-Patent Literature Citations (6)
Entry |
Derwent Abstract J90005-752-B (1990). |
Derwent Abstract J89035-827-B (1989). |
Yoshizaki et al. (nom. Abstr vol. 113 Entry 211864z (1990). |
Schaefer et al. Chem. Abstr vol. 109 entry 170249z (1988). |
Schaefer CA vol. 109 entry 170249Z (1987). |
JP 44-16373 (1969). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
579749 |
Sep 1990 |
|