Canadian Patents Database / Patent 1339132 Summary

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(12) Patent: (11) CA 1339132
(21) Application Number: 611003
(54) English Title: PROSTAGLANDIN DERIVATIVES FOR THE TREATMENT OF GLAUCOMA OR OCULAR HYPERTENSION
(54) French Title: DERIVES DE LA PROSTAGLANDINE POUR LE TRAITEMENT DE GLAUCOME OU DE L'HYPERTENSION OCULAIRE
(52) Canadian Patent Classification (CPC):
  • 167/205
  • 260/235.03
(51) International Patent Classification (IPC):
  • C07C 405/00 (2006.01)
  • A61K 31/557 (2006.01)
(72) Inventors (Country):
  • STJERNSCHANTZ, JOHAN W. (Sweden)
  • RESUL, BAHRAM (Sweden)
(73) Owners (Country):
  • PFIZER HEALTH AB (Sweden)
(71) Applicants (Country):
  • PHARMACIA AB (Sweden)
(74) Agent: RIDOUT & MAYBEE LLP
(45) Issued: 1997-07-29
(22) Filed Date: 1989-09-12
(30) Availability of licence: N/A
(30) Language of filing: English

English Abstract




The invention relates to ophthalmological compositions for
topical treatment of glaucoma or ocular hypertension comprising
an effective intraocular pressure reducing amount of
a prostaglandin derivative of PGA, PGB, PGD, PGE or PGF, in
which the omega chain contains a ring structure, in an
ophthalmologically compatible carrier. The invention further
relates to the preparation of said compositions and their
use for treatment of glaucoma or ocular hypertension.


French Abstract

La présente invention concerne des compositions ophtalmologiques pour le traitement topique de glaucome ou de l'hypertension oculaire, comprenant une quantité efficace réductrice de pression intraoculaire d'un dérivé de prostaglandine de PGA, PGB, PGD, PGE ou PGF, dans laquelle la chaîne oméga contient une structure cyclique, dans un excipient compatible sur le plan ophtalmologique. L'invention concerne en outre la préparation desdites compositions et leur utilisation pour le traitement topique de glaucome ou de l'hypertension oculaire.


Note: Claims are shown in the official language in which they were submitted.


-32-
THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A therapeutic composition for topical treatment of
glaucoma or ocular hypertension, containing a
prostaglandin PGA, PGB, PGD, PGE or PGF in an amount
sufficient to reduce intraocular pressure without causing
substantial ocular irritation and an ophthalmologically
compatible vehicle, which the omega chain of the
prostaglandin has the formula:
(13) (14) (15-24)
C - B - C - D - R2
wherein
C is a carbon atom (the number is indicated within
parenthesis);
B is a single bond, a double bond or a triple bond;
D is a chain with 1-10 carbon atoms, optionally
interrupted by hetero atoms O, S, or N, the substituents
on each carbon atom being H, alkyl groups, lower alkyl
groups with 1-5 carbon atoms, an oxo functionality or a
hydroxyl group;
R2 is a ring structure selected from they group consisting
of phenyl and phenyl having at least one substituent,
said substituent being selected from C1-C5 alkyl groups,
C1-C4 alkoxy groups, trifluoromethyl groups, C1-C3
aliphatic acylamino groups, nitro groups, halogen atoms,
and phenyl group; or an aromatic heterocyclic group
having 5-6 ring atoms, selected from the group consisting
of thiazol, imidazole, pyrrolidine, thiopene and oxazole;
or a cycloalkane or a cycloalkene with 3-7 carbon atoms
in the ring, optionally substituted with lower alkyl
groups with 1-5 carbon atoms.


-33-
2. An ophthalmological composition according to claim
1, wherein D is a chain with 2-8 carbon atoms.
3. An ophthalmological composition according to claim
1, wherein D is a chairs with 2-5 carbon atoms.
4. An ophthalmological composition according to claim
1, wherein D is a chain with 3 carbon atoms.
5. An ophthalmological composition according to claim
1, claim 2, claim 3 or claim 4, wherein B is a single
bond or a double bond and the substituent on C15 being a
carbonyl group or (R)-OH or (S)-OH.
6. An ophthalmological composition according to claim
1, claim 2, claim 3 or claim 4, wherein R2 is a phenyl
group which is unsubstituted or has at least one
substituent selected from C1-C5 alkyl groups, C1-C4 alkoxy
groups, trifluoromethyl groups, C1-C3 aliphatic acylamino
groups, nitro groups, halogen atoms or a phenyl group.
7. An ophthalmological composition according to claim
6, wherein the prostaglandin derivative is a 17-phenyl-
18,19,20-trinor analogue.
8. An ophthalmological composition according to claim
7, wherein the prostaglandin derivative is a 15-dehydro-
17-phenyl-18,19,20-trinor analogue or a 13,14-dihydro-17-
phenyl-18,19,20-trinor analogue.
9. An ophthalmological composition according to claim
8, wherein the prostaglandin derivative is a 13,14-
dihydro-17-phenyl-18,19,20-trinor derivative of PGA, PGE
or PGF.
10. An ophthalmological composition according to claim
8, wherein the prostaglandin derivative is a 15-dehydro-
17-phenyl-18,19,20-trinor derivative of PGA, PGE or PGF.


-34-
11. An ophthalmological composition according to claim
1, claim 2, claim 3, claim 4, claim 7, claim 8, claim 9
or claim 10, wherein the prostaglandin derivative is an
alkyl ester.
12. An ophthalmological composition according to claim
1, wherein the prostaglandin derivative is 13,14-dihydro-
17-phenyl-18,19,20-trinor-PGF2.alpha.-isopropylester.
13. An ophthalmological composition according to claim
1, wherein the prostaglandin derivative is 15-dehydro-17-
phenyl-18,19,20-trinor-PGA2.alpha.-isopropylester.
14. An ophthalmological composition according to claim
1, wherein the prostaglandin derivative is 13,14-dihydro-
17-phenyl-18,19,20-trinor-PGA2-isopropyl-ester.
15. An ophthalmological composition according to claim
1, wherein the prostaglandin derivative is 15-(R)-17-
phenyl-18,19,20-trinor-PGF2.alpha.-isopropylester.
16. An ophthalmological composition according to claim
1, wherein the prostaglandin derivative is 17-phenyl-
18,19,20-trinor-PGF2.alpha.-isopropylester.
17. 13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2.alpha..
18. 13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2.alpha.-alkyl-
ester, in which the alkyl group has 1-10 carbon atoms.
19. Compound of claim 18, wherein the alkyl group is
isopropyl.


-35-
20. The use of a prostaglandin a, b, d, a or f
derivative in which the omega chain of the prostaglandin
has the formula:
(13) (14) (15-24)
C B C - D - R2
wherein
C is a carbon atom (the number is indicated within
parenthesis);
B is a single bond, a double bond or a triple bond;
D is a chain with 1-10 carbon atoms, optionally
interrupted by hetero atoms O, S, or N, the substituents
on each carbon atom being H, alkyl groups, lower alkyl
groups with 1-5 carbon atoms, an oxo functionality or a
hydroxyl group;
R2 is a ring structure selected from the group consisting
of phenyl and phenyl having at least one substituent,
said substituent being selected from C1-C5 alkyl groups,
C1-C4 alkoxy groups, trifluoromethyl groups, C1-C3
aliphatic acylamino groups, nitro groups, halogen atoms,
and phenyl group; or an aromatic heterocyclic group
having 506 ring atoms, selected from the group consisting
of thiazol, imidazole, pyrrolidine, thiopene and oxazole;
or a cycloalkane or a cycloalkene with 3-7 carbon atoms
in the ring, optionally substituted with lower alkyl
groups with 1-5 carbon atoms,
for use in the treatment of glaucoma or ocular
hypertension.
21. The use of a prostaglandin derivative according to
claim 20, wherein D is a chain with 2-8 carbon atoms.
22. The use of a prostaglandin derivative according to
claim 20, wherein D is a chain with 2-5 carbon atoms.
23. The use of a prostaglandin derivative according to
claim 20, wherein D is a chain with 3 carbon atoms.


-36-
24. The use of a prostaglandin derivative according to
claim 20, claim 21, claim 22 or claim 23, wherein B is a
single bond or a double bond and the substituent on C15
being a carbonyl group or (R)-OH or (S)-OH.
25. The use of a prostaglandin derivative according to
claim 20, claim 21, claim 22 or claim 23, wherein R2 is a
phenyl group which is unsubstituted or has at least one
substituent selected from C1-C5 alkyl groups, C1-C4 alkoxy
groups, trifluoromethyl groups, Cl-C3 aliphatic acylamino
groups, nitro groups, halogen atoms or a phenyl group.
26. The use of a prostaglandin derivative according to
claim 25, wherein the prostaglandin derivative is a 17-
phenyl-18,19,20-trinor analogue.
27. The use of prostaglandin derivative according to
claim 26, wherein the prostaglandin derivative is a 15-
dehydro-17-phenyl-18,19,20-trinor analogue or a 13,14-
dihydro-17-phenyl-18,19,20-trinor analogue.
28. The use of a prostaglandin derivative according to
claim 27, wherein the prostaglandin derivative is a
13,14-dihydro-17-phenyl-18,19,20-trinor derivative of
PGA, PGE or PGF.
29. The use of a prostaglandin derivative according to
claim 27, wherein the prostaglandin derivative is a 15-
dehydro-17-phenyl-18,19,20-trinor derivative of PGA, PGE
or PGF.
30. The use of a prostaglandin derivative according to
claim 20, claim 21, claim 22, claim 23, claim 26, claim
27, claim 28 or claim 29, wherein the prostaglandin
derivative is an alkyl ester.


-37-
31. The use of 13,14-dihydro-17-phenyl-18,19,20-trinor-
PGF2.alpha.-isopropylester in the treatment of glaucoma or
ocular hypertension.
32. The use of 15-dehydro-17-phenyl-18,19,20-trinor-
PGA2.alpha.-isopropylester in the treatment of glaucoma or
ocular hypertension.
33. The use of 13,14-dihydro-17-phenyl-18,19,20-trinor-
PGA2-isopropylester in the treatment of glaucoma or
ocular hypertension.
34. The use of 15-(R)-17-phenyl-18,19,20-trinor-PGF2.alpha.-
isopropylester in the treatment of glaucoma or ocular
hypertension.
35. The use of 17-phenyl-18, 19, 20-trinor-PGF2.alpha.-
isopropylester in the treatment of glaucoma or ocular
hypertension.
36. The use of 13,14-dihydro-17-phenyl-18,19,20-trinor-
PGF2.alpha. for the treatment of glaucoma or ocular
hypertension.
37. The use of 13,14-dihydro-17-phenyl-18,19,20-trinor-
PGF2.alpha.-alkyl-ester, in which the alkyl group has 1-10
carbon atoms for the treatment of glaucoma or ocular
hypertension.
38. The use of 13,14-dihydro-17-phenyl-18,19,20-trinor-
PGF2.alpha.-isopropyl-ester in the treatment of glaucoma or
ocular hypertension.


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Admin Status

Title Date
(22) Filed 1989-09-12
(45) Issued 1997-07-29
Expired 2014-07-29

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Filing $0.00 1989-09-12
Maintenance Fee - Patent - Old Act 2 1999-07-29 $100.00 1999-06-18
Maintenance Fee - Patent - Old Act 3 2000-07-31 $100.00 2000-06-19
Maintenance Fee - Patent - Old Act 4 2001-07-30 $100.00 2001-06-20
Registration of Documents $100.00 2001-12-21
Registration of Documents $100.00 2001-12-21
Registration of Documents $100.00 2002-01-10
Section 8 Correction $200.00 2002-06-14
Maintenance Fee - Patent - Old Act 5 2002-07-29 $150.00 2002-06-18
Maintenance Fee - Patent - Old Act 6 2003-07-29 $150.00 2003-06-18
Maintenance Fee - Patent - Old Act 7 2004-07-29 $200.00 2004-06-18
Maintenance Fee - Patent - Old Act 8 2005-07-29 $200.00 2005-06-20
Maintenance Fee - Patent - Old Act 9 2006-07-31 $200.00 2006-06-16
Maintenance Fee - Patent - Old Act 10 2007-07-30 $250.00 2007-06-07
Maintenance Fee - Patent - Old Act 11 2008-07-29 $250.00 2008-06-18
Maintenance Fee - Patent - Old Act 12 2009-07-29 $250.00 2009-06-19
Maintenance Fee - Patent - Old Act 13 2010-07-29 $250.00 2010-06-18
Maintenance Fee - Patent - Old Act 14 2011-07-29 $250.00 2011-06-22
Maintenance Fee - Patent - Old Act 15 2012-07-30 $450.00 2012-06-19
Maintenance Fee - Patent - Old Act 16 2013-07-29 $450.00 2013-06-20
Registration of Documents $100.00 2014-11-06

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Description 1997-05-30 35 1,232
Cover Page 2002-07-02 2 41
Claims 2002-07-02 6 255
Cover Page 2002-07-19 2 44
Cover Page 1997-12-08 1 17
Abstract 1997-05-30 1 14
Claims 1997-05-30 6 203
Correspondence 2002-06-14 25 1,028
Prosecution-Amendment 2002-07-02 2 45
Prosecution-Amendment 2002-07-19 2 47
Prosecution-Amendment 2006-10-23 1 22
Correspondence 2006-11-01 1 12
Correspondence 2015-08-25 1 21