USRE32112E - Spironolactone-containing composition and use thereof - Google Patents
Spironolactone-containing composition and use thereof Download PDFInfo
- Publication number
- USRE32112E USRE32112E US06/596,290 US59629084A USRE32112E US RE32112 E USRE32112 E US RE32112E US 59629084 A US59629084 A US 59629084A US RE32112 E USRE32112 E US RE32112E
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- United States
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- composition
- spironolactone
- iaddend
- iadd
- carrier
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 title claims abstract description 37
- 229960002256 spironolactone Drugs 0.000 title claims abstract description 36
- 230000001548 androgenic effect Effects 0.000 claims abstract description 16
- 206010020112 Hirsutism Diseases 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
- 235000019271 petrolatum Nutrition 0.000 claims description 5
- 239000003871 white petrolatum Substances 0.000 claims description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 3
- 238000004945 emulsification Methods 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- -1 propylhyroxybenzoate Substances 0.000 claims description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
- 229960003415 propylparaben Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 7
- 239000003208 petroleum Substances 0.000 claims 1
- 239000003098 androgen Substances 0.000 abstract description 6
- 229940030486 androgens Drugs 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 230000002280 anti-androgenic effect Effects 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 230000003676 hair loss Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- 230000027758 ovulation cycle Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 206010001367 Adrenal insufficiency Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010065371 Hyperthecosis Diseases 0.000 description 1
- 206010024870 Loss of libido Diseases 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 208000017515 adrenocortical insufficiency Diseases 0.000 description 1
- 229940092229 aldactone Drugs 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 229940124624 oral corticosteroid Drugs 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
Definitions
- the present invention relates to a composition containing spironolactone, and more particularly, to such a composition containing spironolactone for application directly to human skin for effectively suppressing excess androgenic activity at the skin site.
- Cyproterone acetate has been orally administered to treat hirsuitism and has proved effective therein.
- severe side effects such as, adrenal insufficiency and loss of libido have rendered its use undesirable.
- Oral contraceptives and corticosteroids have also been utilized for treatment with androgenic access, although numerous side effects have minimized the use thereof.
- Spironolactone has also been orally administered for treatment of excess androgens in women. However, when spironolactone is administered orally, the concentration of spironolactone must be increased to a level at which equal concentrations are provided to all tissue even though specific skin tissue at which excess androgenic activity occurs may be the only desired area to be treated.
- spironolactone is administered orally on a daily basis, side effects, such as, metrorrhagia (i.e., disruption of the menstrual cycle during which non-menstrual bleeding from the uterus occurs) and electrolytic disturbance involving potassium accumulation in the blood, may occur.
- metrorrhagia i.e., disruption of the menstrual cycle during which non-menstrual bleeding from the uterus occurs
- electrolytic disturbance involving potassium accumulation in the blood may occur.
- oral ingestion of spironolactone must be constantly monitored by a licensed physician which is both costly and time consuming.
- spironolactone should only be orally administered to women between the fifth and twenty second day of their menstrual cycle to aovid metrorrahgia, a woman must constantly be appraised of and cognizant of this fact.
- large amounts of tissue which are not afflicted with an excess of androgenic activity are unnecessarily intoxicated with spironolactone.
- composition possessing antiandrogenic activity which can be applied directly to human skin for effectively suppressing the excess androgenic activity thereof.
- the present invention relates to a spironolactone containing composition for effectively suppressing excess androgenic activity which occurs at a skin site to effectively treat, inter alia, hirsuitism.
- the composition consists essentially of an effective amount of spironolactone incorporated into a carrier.
- a solubilizer, a viscosifier and a preservative may also be selectively incorporated into the composition of the present invention as desired.
- the present invention relates to a spironolactone-containing composition for application to an area of human skin afflicted with hirsuitism for effective treatment thereof.
- Applicant has discovered that by direct application of spironolactone to an afflicted area of human skin via a suitable carrier, hirsuitism in the afflicted area is effectively controlled and reduced while substantially eliminating any side effects attendant with use of spironolactone. It is believed that spironolactone suppresses androgenic activity in the skin which is a major site of androgene metabolism.
- the composition of the present invention comprises an effective amount of spironolactone and a suitable .[.liquid.]. carrier.
- spironolactone refers to aldactone [3-(3-oxo-7-acethylthio-17-hydroxy-antrost-4-en-17-4yl) propionic acid lactone].
- the .[.liquid.]. carrier can be any .[.liquid.]. carrier which can function to transport an active ingredient to the area of human skin to be treated and preferably which is capable of being rubbed into the skin so as to be transparent in appearance.
- Exemplary .[.liquid.]. carriers are alcohol, urea, mineral oil and white petrolatum.
- the composition of the present invention can have characteristics ranging from those of a cream to an ointment.
- spironolactone is incorporated into the composition of the present invention in the amount of from about 0.25 wt. % to about 2.0 wt. %, and most preferably about 1.0 wt. %.
- Spironolactone can be incorporated into a suitable carrier in a preselected amount as dictated by the concentration ranges just described.
- a solubilizer such as, stearyl alcohol, or cetyl alcohol, can be utilized in the composition of the present invention to solubilize spironolactone therein so as to aid incorporation of spironolactone into the carrier.
- the solubilizer can be incorporated into the composition of the present invention in an amount of from about 1.5 wt. % to about 3.0 wt. %.
- a viscosifier such as, cottonseed oil, can also be incorporated into the composition of the present invention where a lower viscosity is desirable and/or to aid in emulsification of the solubilizer within the carrier.
- the viscosifier can be incorporated into the composition of the present invention in an amount of from about 3 wt.
- a preservative such as, methylhydroxybenzoate, propylhydroxybenzoate, or mixtures thereof, can also be incorporated into the composition of the present invention in an amount from about 0.25 wt. % to about 0.50 wt. %.
- the preferred composition of the present invention is about 1.0 wt. % spironolactone, about 1.5 wt. % stearyl alcohol, about 3.0 wt. % cottonseed oil, about 0.25 wt. % methylhydroxybenzoate, and about 94.25 wt. % white petrolatum.
- the composition of the present invention may be manually applied to the afflicted area of skin and rubbed until absorbed fully into the area. Concomitant with a reduction of hirsuitism in the area treated, is an improvement of acne which is also a disorder known to be androgen dependent.
- the entire physical system of an individual treated is not intoxicated with spironolactone but only that surface skin area to be treated, thus minimizing side effects attendant with application of spironolactone and constant physician monitoring which is attendent with oral ingestion of spironolactone.
- the composition of the present invention has been described as effective in treating hirsuitism in women, the composition is also effective in retarding baldness in men since such baldness is characterized by excess andgrogenic activity.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
A composition containing spironolactone in an amount effective to suppress excess androgenic activity. The spironolactone-containing composition is applied directly to the skin site afflicted with excess androgens.
Description
I. Technical Field
The present invention relates to a composition containing spironolactone, and more particularly, to such a composition containing spironolactone for application directly to human skin for effectively suppressing excess androgenic activity at the skin site.
II. Background Art
In most physically normal women, androgens or male sex homones are effectively synthesized by both ovaries and adrenals. However, in certain females afflicted with polycystic ovarian disease or ovarian hyperthecosis, the ovaries appear to be the major source of enhanced androgen secretion, especially testosterone. Such excess androgen secretion in women has been linked to increased masculine characteristics, in particular, hirsuitism.
A number of prior art compounds possessing antiandrogenic activity have been utilized in treatment of hirsuitism, as detailed in: A Novel Use of Spironolactone; Treatment of Hirsuitism, "Journal of Clinical Endocrinology and Metabolism" Shapiro, et al., Vol. 51, No. 3, pp. 429-432, Jan. 4, 1980; Spironolactone Therapy for Hirsuitism in a Hyper androgenic Woman, "Annals of Internal Medicine", Ober, et al., Vol. 89, No. 5 (Part 1), pp. 643, 644, November, 1978; and New Therapeutic Approach to the Hirsute Patient, "Fertility and Sterility", Boiselle, et al., Vol. 32, No. 3, pp. 276-279, September, 1979. Cyproterone acetate has been orally administered to treat hirsuitism and has proved effective therein. However, severe side effects, such as, adrenal insufficiency and loss of libido have rendered its use undesirable. Oral contraceptives and corticosteroids have also been utilized for treatment with androgenic access, although numerous side effects have minimized the use thereof. Spironolactone has also been orally administered for treatment of excess androgens in women. However, when spironolactone is administered orally, the concentration of spironolactone must be increased to a level at which equal concentrations are provided to all tissue even though specific skin tissue at which excess androgenic activity occurs may be the only desired area to be treated. If spironolactone is administered orally on a daily basis, side effects, such as, metrorrhagia (i.e., disruption of the menstrual cycle during which non-menstrual bleeding from the uterus occurs) and electrolytic disturbance involving potassium accumulation in the blood, may occur. Thus, oral ingestion of spironolactone must be constantly monitored by a licensed physician which is both costly and time consuming. In addition, as spironolactone should only be orally administered to women between the fifth and twenty second day of their menstrual cycle to aovid metrorrahgia, a woman must constantly be appraised of and cognizant of this fact. Finally, even when spironolatone is properly administered orally, large amounts of tissue which are not afflicted with an excess of androgenic activity are unnecessarily intoxicated with spironolactone.
Thus, it can be appreciated that a need exists for a composition possessing antiandrogenic activity which can be applied directly to human skin for effectively suppressing the excess androgenic activity thereof.
The present invention relates to a spironolactone containing composition for effectively suppressing excess androgenic activity which occurs at a skin site to effectively treat, inter alia, hirsuitism. The composition consists essentially of an effective amount of spironolactone incorporated into a carrier. A solubilizer, a viscosifier and a preservative may also be selectively incorporated into the composition of the present invention as desired.
The present invention relates to a spironolactone-containing composition for application to an area of human skin afflicted with hirsuitism for effective treatment thereof. Applicant has discovered that by direct application of spironolactone to an afflicted area of human skin via a suitable carrier, hirsuitism in the afflicted area is effectively controlled and reduced while substantially eliminating any side effects attendant with use of spironolactone. It is believed that spironolactone suppresses androgenic activity in the skin which is a major site of androgene metabolism.
The composition of the present invention comprises an effective amount of spironolactone and a suitable .[.liquid.]. carrier. As utilized throughout the description, the term "spironolactone" refers to aldactone [3-(3-oxo-7-acethylthio-17-hydroxy-antrost-4-en-17-4yl) propionic acid lactone]. The .[.liquid.]. carrier can be any .[.liquid.]. carrier which can function to transport an active ingredient to the area of human skin to be treated and preferably which is capable of being rubbed into the skin so as to be transparent in appearance. Exemplary .[.liquid.]. carriers are alcohol, urea, mineral oil and white petrolatum. Depending upon the exact .[.liquid.]. carrier employed and the addition of any viscosifiers, the composition of the present invention can have characteristics ranging from those of a cream to an ointment.
In accordance with the preferred embodiment, spironolactone is incorporated into the composition of the present invention in the amount of from about 0.25 wt. % to about 2.0 wt. %, and most preferably about 1.0 wt. %. Spironolactone can be incorporated into a suitable carrier in a preselected amount as dictated by the concentration ranges just described.
A solubilizer, such as, stearyl alcohol, or cetyl alcohol, can be utilized in the composition of the present invention to solubilize spironolactone therein so as to aid incorporation of spironolactone into the carrier. The solubilizer can be incorporated into the composition of the present invention in an amount of from about 1.5 wt. % to about 3.0 wt. %. A viscosifier, such as, cottonseed oil, can also be incorporated into the composition of the present invention where a lower viscosity is desirable and/or to aid in emulsification of the solubilizer within the carrier. The viscosifier can be incorporated into the composition of the present invention in an amount of from about 3 wt. % to about 6 wt. %. A preservative, such as, methylhydroxybenzoate, propylhydroxybenzoate, or mixtures thereof, can also be incorporated into the composition of the present invention in an amount from about 0.25 wt. % to about 0.50 wt. %.
The preferred composition of the present invention is about 1.0 wt. % spironolactone, about 1.5 wt. % stearyl alcohol, about 3.0 wt. % cottonseed oil, about 0.25 wt. % methylhydroxybenzoate, and about 94.25 wt. % white petrolatum.
The composition of the present invention may be manually applied to the afflicted area of skin and rubbed until absorbed fully into the area. Concomitant with a reduction of hirsuitism in the area treated, is an improvement of acne which is also a disorder known to be androgen dependent. Thus, it can be appreciated that in utilizing the spironolactone-containing composition of the present invention, the entire physical system of an individual treated is not intoxicated with spironolactone but only that surface skin area to be treated, thus minimizing side effects attendant with application of spironolactone and constant physician monitoring which is attendent with oral ingestion of spironolactone. And although the composition of the present invention has been described as effective in treating hirsuitism in women, the composition is also effective in retarding baldness in men since such baldness is characterized by excess andgrogenic activity.
While various embodiments and modifications of the invention have been described in the foregoing description, further modifications will be apparent to those skilled in the art. Such modifications are included within the scope of this invention as defined by the following claims.
Claims (10)
1. A composition for effectively suppressing excess androgenic activity which occurs at a skin site so as to effectively treat .[.hirsuitisum.]. .Iadd.hirsutism, .Iaddend.said composition being .[.directly applied.]. .Iadd.in a form suitable for direct application .Iaddend.to said skin site .[., the composition.]. .Iadd.and .Iaddend.consisting essentially of .[.: a liquid carrier selected from the group consisting of alcohol, urea, mineral oil and white petrolatum; and .]. spironolactone in an amount of from about 0.25 wt. % to about 5.0 wt. %.Iadd., .Iaddend.which effectively suppresses excess androgenic activity at said skin site.Iadd., in a suitable carrier therefor; said composition having characteristics ranging from those of a cream to those of an ointment. .Iaddend.
2. The composition of claim 1 wherein .[.said liquid.]. .Iadd.the .Iaddend.carrier is white petrolatum.
3. The composition of claim 1 further consisting essentially of:
a solubilizer selected from the group consisting of stearyl alcohol, cetyl alcohol or mixtures thereof, said solubilizer being present in an amount of from about 1.5 wt. % to about 3.0 wt. % so as to aid incorporation of said spironolactone into said carrier.
4. The composition of claim 3 further consisting essentially of a viscosifier in an amount sufficient to aid in emulsification of said solubilizer in said carrier.
5. The composition of claim 1 further consisting essentially of:
a preservative selected from the group consisting of methylhydroxybenzoate, propylhyroxybenzoate, or mixtures thereof, said preservative being employed in an amount sufficient to extend the useful like of said composition.
6. In a process for treating at least one skin site characterized by excess androgenic activity so as to effectively suppress said excess androgenic activity, the improvement comprising: directly applying a spironolactone-containing composition to said at least one skin site, said composition consisting essentially of .[.a liquid carrier selected from the group consisting of alcohol, urea, mineral oil and white petroleum and.]. spironolactone in an amount of from about 0.25 wt. % to about 5.0 wt. % .Iadd.in a suitable carrier therefor, .Iaddend.which effectively suppresses androgenic activity at said skin site.
7. The process of claim 6 wherein said .[.liquid.]. carier is white petrolatum.
8. The process of claim 6 wherein said composition further consists essentially of a solubilizer selected from the group consisting of stearyl alcohol, cetyl alcohol or mixtures thereof, said solubilizer being present in an amount of from about 1.5 wt. % to about 3.0 wt. % so as to aid incorporation of said spironolactone into said carrier.
9. The process of claim 8 wherein said composition further consists essentially of a viscosifier in an amount sufficient to aid in emulsification of said solubilizer in said carrier.
10. The process of claim 6 wherein said composition further consists essentially of a preservative selected from the group consisting of methylhydroxybenzoate, propylhydroxybenzoate, or mixtures thereof, said preservative being employed in an amount sufficient to extend the useful life of said composition. .Iadd.11. The process according to claim 6 for the treatment of hirsutism caused by excess androgenic activity. .Iaddend. .Iadd.12. The process according to claim 6 for the treatment of acne caused by excess androgenic activity. .Iaddend.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/596,290 USRE32112E (en) | 1981-05-26 | 1984-04-03 | Spironolactone-containing composition and use thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/266,924 US4347245A (en) | 1981-05-26 | 1981-05-26 | Spironolactone-containing composition and use thereof |
| US06/596,290 USRE32112E (en) | 1981-05-26 | 1984-04-03 | Spironolactone-containing composition and use thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/266,924 Reissue US4347245A (en) | 1981-05-26 | 1981-05-26 | Spironolactone-containing composition and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE32112E true USRE32112E (en) | 1986-04-15 |
Family
ID=26952110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/596,290 Expired - Lifetime USRE32112E (en) | 1981-05-26 | 1984-04-03 | Spironolactone-containing composition and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE32112E (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050282253A1 (en) * | 1995-10-23 | 2005-12-22 | Folkman M J | Therapeutic antiangiogenic endostatin compositions |
| US10350223B2 (en) | 2015-03-03 | 2019-07-16 | Richard W. Yee | Compositions and methods for treating ocular diseases |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3257390A (en) * | 1963-06-12 | 1966-06-21 | Merck & Co Inc | Ring a unsaturated 21-hydroxy-3-oxo-17alpha-pregnane-17-carboxylic acid lactone diuretic agents |
-
1984
- 1984-04-03 US US06/596,290 patent/USRE32112E/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3257390A (en) * | 1963-06-12 | 1966-06-21 | Merck & Co Inc | Ring a unsaturated 21-hydroxy-3-oxo-17alpha-pregnane-17-carboxylic acid lactone diuretic agents |
Non-Patent Citations (8)
| Title |
|---|
| Boisselle et al., "Fertility and Sterility; vol. 32, No. 3, Sep. 1979, pp. 276-279. |
| Boisselle et al., Fertility and Sterility; vol. 32, No. 3, Sep. 1979, pp. 276 279. * |
| Chem. Abst. 83(21) 172,881t, An Abstract of the Publication in "Endocrinology", 97(1) pp. 52-58. |
| Chem. Abst. 83(21) 172,881t, An Abstract of the Publication in Endocrinology , 97(1) pp. 52 58. * |
| Ober et al., "Annals of Internal Medicine" 89 No. 5 (Part 1) Nov. 1978, pp. 543-544. |
| Ober et al., Annals of Internal Medicine 89 No. 5 (Part 1) Nov. 1978, pp. 543 544. * |
| Shapiro et al., "Journal of Clinical Endocrinology and Metabolism, 51; p. 429 (1980). |
| Shapiro et al., Journal of Clinical Endocrinology and Metabolism, 51; p. 429 (1980). * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050282253A1 (en) * | 1995-10-23 | 2005-12-22 | Folkman M J | Therapeutic antiangiogenic endostatin compositions |
| US7495089B2 (en) | 1995-10-23 | 2009-02-24 | The Children's Medical Center Corporation | Therapeutic antiangiogenic endostatin compositions |
| US20090137518A1 (en) * | 1995-10-23 | 2009-05-28 | The Children's Medical Center Corporation | Therapeutic Antiangiogenic Endostatin Compositions |
| US7867975B2 (en) | 1995-10-23 | 2011-01-11 | The Children's Medical Center Corporation | Therapeutic antiangiogenic endostatin compositions |
| US10350223B2 (en) | 2015-03-03 | 2019-07-16 | Richard W. Yee | Compositions and methods for treating ocular diseases |
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