Claims
- 1. A compound of Formula 1.0: ##STR14## 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) (2-chloro-4-methoxyphenoxy)propoxymethyl;
- (8) --(CH.sub.2).sub.a R.sup.16 wherein a is an integer of 1 to 6 and R.sup.16 is selected from the group consisting of --C(O)OR.sup.17, --OR.sup.17, --R.sup.17, and --N(R.sup.17).sub.2, wherein each R.sup.17 can be the same or different and is selected from the group consisting of alkyl, alkenyl and H;
- (9) H; and
- (10) --OR.sup.18 wherein R.sup.18 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 selected from the group consisting of:
- (1) alkyl;
- (2) haloalkenyl wherein the halogen atoms are selected from the group consisting of F, Cl, Br and I;
- (3) --(CH.sub.2).sub.a NR.sup.6 R.sup.7 wherein a is an integer from 1 to 6, and R.sup.6 and R.sup.7 are the same or different and are selected from the group consisting of H and alkyl; and
- (4) acyl having the formula --C(O)R.sup.8 wherein R.sup.8 is selected from the group consisting of H, alkyl, phenyl, --CH.sub.2 --phenyl, alkenyl, and substituted alkyl;
- (D) Each R.sup.2 for each m is independently selected from the group consisting of:
- (1) alkyl;
- (2) alkoxy;
- (3) phenyloxy;
- (4) phenyl;
- (5) phenylalkyloxy
- (6) halogen atoms selected from the group consisting of F, Cl, Br and I;
- (7) --O--CO--R.sup.10 wherein R.sup.10 is alkyl--which may be substituted with OH, SH, NH.sub.2 and/or halogen--, --CH.sub.2 --phenyl, alkenyl;
- (8) --N(R.sup.11).sub.2 wherein each R.sup.11 is independently selected from the group consisting of H, alkyl, and R.sup.12 C(O)-- wherein R.sup.12 is as above defined
- (9) --OH;
- (10) --CH.sub.2 OH;
- (11) --COOH;
- (12) --COOR.sup.13, wherein R.sup.13 is alkyl;
- (13) --SO.sub.3 H;
- (14) --SO.sub.2 NHR.sup.14, wherein R.sup.14 is selected from the group consisting of alkyl; and H;
- (15) --PO.sub.3 H;
- (16) --PO(OR.sup.15).sub.2, wherein R.sup.15 is alkyl;
- (17) --OPO.sub.3 H;
- (18) --OP(OR.sup.15).sub.2 wherein R.sup.15 is as above defined;
- (19) --CF.sub.3 ; and
- (20) CONH.sub.2 ;
- (E) m is 0 or an integer from 1 to 2; and
- (F) R.sup.4 and R.sup.5 are the same and are selected from the group consisting of:
- (1) alkyl; and
- (2) acyl having the formula --C(O)R.sup.8
- wherein R.sup.8 is selected from the group consisting of H, alkyl, alkenyl, and substituted alkyl;
- and wherein
- acyl represents a group having the formula --C(O)R.sup.8 wherein R.sup.8 is selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and substituted alkyl;
- alkenyl represents straight and branched aliphatic hydrocarbon groups having 1 double carbon-to-carbon double 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 aliphatic hydrocarbon groups having from 1 to 6 carbon atoms;
- haloalkenyl represents an alkenyl group, as defined above, wherein one hydrogen atom is replaced by a halogen atom;
- alkynyl represents a straight or branched aliphatic hydrocarbon group having one carbon-to-carbon triple bond, and having from 3 to 8 carbon atoms;
- 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;
- 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, --OH, --O--alkyl, --NH.sub.2, --N(alkyl).sub.2 wherein each alkyl group is the same or different, --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, is as above defined; and
- substituted phenyl represents a phenyl group, as defined above, wherein one or two of the H atoms attached to the ring carbon atoms is replaced by a group independently selected from the group consisting of halo, alkyl, hydroxy, alkoxy, phenoxy, amino, alkylamino, and dialkylamino;
- together with the pharmaceutically acceptable salts of the compounds of Formula 1.0 that are acidic or basic.
- 2. A compound of claim 1 wherein R.sup.4 and R.sup.5 are acyl.
- 3. A compound of claim 2 wherein R.sup.1 is acyl.
- 4. A compound of claim 2 wherein R.sup.1 is alkyl.
- 5. 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) CI;
- (6) F; and
- (7) I.
- 6. A compound of claim 1 wherein R.sup.3 is selected from the group consisting of:
- (1) --CH.sub.3 ;
- (2) --O.sub.6 H.sub.13 ;
- (3) --C.sub.7 H.sub.15 ;
- (4) --CH.sub.2 -phenyl;
- (5)
- (6) phenyl;
- (7) ##STR15## (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.
- 7. A compound of claim 1 wherein:
- (B) 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; and
- (7) I; and
- (C) 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;
- (5)
- (6) --phenyl; ##STR16## (7) (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.
- 8. A compound of claim 7 wherein R.sup.4 and R.sup.5 are acyl and R.sup.1 is alkyl.
- 9. The compound of claim 7 wherein R.sup.4, R.sup.5 and R.sup.1 are the same acyl group.
- 10. A compound as claimed in claim 1, wherein R.sup.3 is selected from 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; ##STR17## (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 ;
- R.sup.2 is selected from the group consisting of:
- (1) --OH.sub.3 ;
- (2) --OCH.sub.3 ;
- (3) --OCOC H.sub.3 ;
- (4 ) --OCH.sub.2 --phenyl;
- (5) Cl;
- (6) F; and
- (7) I; and
- m is 0, 1 or 2;
- R.sup.4 and R.sup.5 are selected from the group consisting of acetyl, 1-oxopentyl, 1-oxopropyl, and methyl; and
- R.sup.1 is selected from the group consisting of methyl, acetyl, 1-oxopentyl, and 1-oxopropyl.
- 11. A compound as claimed in 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;
- (5) --CH.sub.2 CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 ;
- (6) --phenyl; and ##STR18## R.sup.2 is selected from the group consisting of: (1) --CH.sub.3 ;
- (2) --OCOCH.sub.3 ; and
- (3) --OCH.sub.2 --phenyl; and
- m is 0, 1 or 2;
- R.sup.4 and R.sup.5 are selected from the group consisting of acetyl, 1-oxopentyl, 1-oxopropyl, and methyl; and
- R.sup.1 is selected from the group consisting of methyl, acetyl, 1-oxopentyl, and 1-oxopropyl.
- 12. A compound selected from the group consisting of ##STR19## or a pharmaceutically acceptable salt thereof.
- 13. A pharmaceutical composition comprising an effective amount of a pharmaceutically acceptable carder and an antivirally effective amount of a compound of claim 1.
- 14. A pharmaceutical composition comprising an effective amount of a pharmaceutically acceptable carder and an antivirally effective amount of a compound of claim 12.
Parent Case Info
The present application is the United States national application corresponding to International Application No. PCT/U.S. 91/06253, filed Sept. 6, 1991 and designating the United States, which PCT application is in turn a continuation-in-part of U.S. application Ser. No. 07/579744 , filed Sept. 7, 1990, now abandoned, 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/US91/06251 |
9/6/1991 |
|
|
3/1/1993 |
3/1/1993 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO92/04326 |
3/19/1992 |
|
|
US Referenced Citations (8)
Foreign Referenced Citations (2)
Number |
Date |
Country |
578536 |
Aug 1976 |
CHX |
9204326 |
Mar 1992 |
WOX |
Non-Patent Literature Citations (6)
Entry |
Derwent Abstract J90005-752-B (1990). |
Derwent Abstract J89035-827-B (1980). |
Yoshizaki Chem. Abstr., vol. 113, entry 211864Z (1990). |
Schaefer, Chem. Abstr., vol. 109 entry 170249Z (1988). |
Chem. Abstr., vol. 114 (1991), entry 143242P. |
Schaefer et al. Chem. abstr. vol. 109 Entry 170249 (1988). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
579744 |
Sep 1990 |
|