Claims
- 1. A compound of formula (I) ##STR54## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkenyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy, or R.sub.2 and R.sub.5, taken together form an oxo group; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR55## or the radical ##STR56## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of
- (a') hydrogen and
- (b') C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts.
- 2. 6.beta.H-6(9.alpha.)-oxide-11.alpha., 15S-dimethoxy-16(S,R)-fluoro-20-methyl-prost-13-ynoic acid methyl ester.
- 3. A compound having the formula (I) ##STR57## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy, or R.sub.2 and R.sub.5, taken together form an oxo group; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR58## or the radical ##STR59## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 4. A compound having the formula (I) ##STR60## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen or hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR61## or the radical ##STR62## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of
- (a') hydrogen and
- (b') C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 5. A compound selected from the group consisting of:
- 6.beta.H-6(9.alpha.)-oxide-15S-methoxy-16S-methyl-prost-13-ynoic acid methyl ester;
- 6.beta.H-6(9.alpha.)-oxide-15S-methoxy-16S-methyl-prost-13-ynoic acid;
- 6.beta.H-6(9.alpha.)-oxide-15-methoxy-prost-13-ynoic acid; and the 6.alpha.H-diastereoisomer thereof;
- 11.alpha.-hydroxy-15S-methoxy-6.beta.H-6(9.alpha.)-oxide-16S-methyl-prost-13-ynoic acid methyl ester;
- 11.alpha.-hydroxy-15S-ethoxy-6.beta.H-6(9.alpha.)-oxide-16S-methyl-prost-13-ynoic acid ethyl ester,
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 6. A compound having the formula (I) ##STR63## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7
- q is 1;
- R.sub.1 is hydrogen, hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR64## or the radical ##STR65## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 7. A compound having the formula (I) ##STR66## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen, hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR67## or the radical ##STR68## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of
- (a') hydrogen and
- (b') C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 8. A compound having the formula (I) ##STR69## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is hydrogen;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen, hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR70## or the radical ##STR71## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 9. A compound having the formula (I) ##STR72## wherein R is carboxy or a C.sub.1 -C.sub.12 carbalkoxy group;
- Z.sub.1 is bromine or chlorine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR73## or the radical ##STR74## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, --S--and --(CH.sub.2).sub.m, wherein m is zero or 1; R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 10. A compound having the formula (I) ##STR75## wherein R is carboxy or a C.sub.1 -C.sub.12 carbalkoxy group;
- Z.sub.1 is bromine or chlorine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen, or benzyloxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR76## or the radical ##STR77## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m --, wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of:
- (a) hydrogen and
- (b) C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 11. A compound having the formula (I) ##STR78## wherein R is carboxy or a C.sub.1 -C.sub.12 carbalkoxy group;
- Z.sub.1 is bromine or chlorine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydroxy, or C.sub.1 -C.sub.6 alkoxy;
- Y is --C.uparw.C--; one of R.sub.2 and R.sub.5 is C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical
- or the radical
- each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m --, wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of: (a) hydrogen and (b) C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 12. A compound having the formula (I)
- wherein
- R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is iodine;
- p is zero or an integer of 1 to 7;
- q is 1,
- R.sub.1 is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- Y is --C.uparw.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy, or R.sub.2 and R.sub.5, taken together form an oxo group; each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical
- or the radical
- each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 13. A compound having the formula (I)
- wherein
- R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is iodine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen, or hydroxy,
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR79## or the radical ##STR80## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of
- (a') hydrogen and
- (b') C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 14. A compound having the formula (I) ##STR81## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is iodine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen or hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, and the other is C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR82## or the radical ##STR83## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --O--, of --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 15. A compound having the formula (I) ##STR84## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is iodine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen or hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR85## or the radical ##STR86## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is a member selected from the group consisting of
- (a') hydrogen and
- (b') C.sub.1 -C.sub.4 alkyl;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 16. A compound having the formula (I) ##STR87## wherein R is --COOR.sub.c where R.sub.c is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- Z.sub.1 is iodine;
- p is zero or an integer of 1 to 7;
- q is 1;
- R.sub.1 is hydrogen or hydroxy;
- Y is --C.tbd.C--;
- one of R.sub.2 and R.sub.5 is C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or phenyl, .alpha.-naphthyl or .beta.-naphthyl, and the other is hydroxy, C.sub.1 -C.sub.6 alkoxy, or benzyloxy;
- each of R.sub.3 and R.sub.4, which are the same or different, may be hydrogen, C.sub.1 -C.sub.6 alkyl or fluorine or R.sub.3 and R.sub.4, taken together with the carbon atom to which they are linked, form the radical ##STR88## or the radical ##STR89## each of n.sub.1 and n.sub.2, which are the same or different, is zero or an integer of 1 to 6;
- X is a member selected from the group consisting of --0--, --S-- and --(CH.sub.2).sub.m -- wherein m is zero or 1;
- R.sub.6 is phenyl, .alpha.-naphthyl or .beta.-naphthyl, unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoxy;
- and the pharmaceutically or veterinarily acceptable salts thereof.
- 17. A pharmaceutical or veterinary composition, suitable for use as a hypotensive agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 18. A pharmaceutical or veterinary composition, suitable for use as a vasodilatory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 19. A pharmaceutical or veterinary composition, suitable for use as an anti-aggregating agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 20. A pharmaceutical or veterinary composition, suitable for use as an anti-thrombotic agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 21. A pharmaceutical or veterinary composition, suitable for use as a luteolytic agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 22. A pharmaceutical or veterinary composition, suitable for use as a cytoprotective agent active on the mucous membranes of the gastrointestinal tract, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 23. A pharmaceutical or veterinary composition, suitable for use as an anti-secretory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 24. A pharmaceutical or veterinary composition, suitable for use as a bronchodilatory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 25. A pharmaceutical or veterinary composition, suitable for use as an anti-asthmatic agent, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
- 26. A pharmaceutical or veterinary composition, suitable for use as an uterus stimulant, said composition comprising a therapeutically effective amount of a compound as claimed in any of claims 1 to 16, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Priority Claims (5)
| Number |
Date |
Country |
Kind |
| 31401 A/76 |
Dec 1976 |
ITX |
|
| 19283 A/77 |
Jan 1977 |
ITX |
|
| 21171 A/77 |
Mar 1977 |
ITX |
|
| 21412 A/77 |
Mar 1977 |
ITX |
|
| 21863 A/77 |
Mar 1977 |
ITX |
|
Parent Case Info
This is a divisional application of Ser. No. 928,809, pending, filed July 28, 1978, which is a divisional of Ser. No. 859,703 filed Dec. 12, 1977, now abandoned.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
| 4125712 |
Axen |
Nov 1979 |
|
Divisions (2)
|
Number |
Date |
Country |
| Parent |
928809 |
Jul 1978 |
|
| Parent |
859703 |
Dec 1977 |
|
Patent Grant
4259244
