WO1999012535A1 - Utilisation de derives de benzene sulfonamide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie - Google Patents
Utilisation de derives de benzene sulfonamide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie Download PDFInfo
- Publication number
- WO1999012535A1 WO1999012535A1 PCT/FR1998/001927 FR9801927W WO9912535A1 WO 1999012535 A1 WO1999012535 A1 WO 1999012535A1 FR 9801927 W FR9801927 W FR 9801927W WO 9912535 A1 WO9912535 A1 WO 9912535A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- alkyl
- aspermia
- branched
- linear
- Prior art date
Links
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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
Definitions
- the subject of the present invention is the use of benzene sulfona ide derivatives, described in patent application WO97 / 06136, to obtain a medicament intended for the treatment of retrograde aculation or aspermia.
- R x represents a hydrogen or halogen atom, such as chlorine or fluorine, a group C 1 . 4 alkyl or C 1 . 4 alkoxy, linear or branched, preferably a group C 1 . 4 alkoxy and more particularly methoxy,
- R 2 , R 3 , and R 4 represent, independently of each other, a hydrogen atom, a C 1 _ i alkyl group, linear or branched, or a C 3 group.
- 4 cycloalkyl and R 5 represents a hydrogen atom, a group C x . 2 alkyl, C - 2 fluoroalkyle or C 1-2 perfluoroalkyle, preferably a hydrogen or a methyl.
- the compounds of general formula (I) can comprise one or more asymmetric carbon atoms. They can therefore exist in the form of enantiomers or diastereoisomers. These enantiomers, diastereoisomers, as well as their mixtures, including racemic mixtures, form part of the invention.
- the compounds of general formula (I) can be in the form of a free base or of addition salts with pharmaceutically acceptable acids, which also form part of the invention.
- the table below illustrates the structures of some compounds which can be used according to the invention.
- iC 3 H 7 represents an isopropyl, tC 4 H 9 a tert-butyl, cC 3 H 5 or cyclopropyl; ( ⁇ ) represents a racemic; (+) represents the dextrorotatory enantiomer; (-) represents the levorotatory enantiomer; anti represents a mixture of RS and SR diastereoisomers; syn represents a mixture of RR and SS diastereoisomers.
- the compounds of the invention were subjected to biological tests intended to demonstrate their contractile activity on the smooth muscles of the trigone and the arteries.
- the in vitro activity of the compounds of the invention was studied on the smooth muscles of the trigone and arteries. These tests were carried out on male New Zealand rabbits weighing from 3 to 3.5 kg. The animals were killed by cervical dislocation, and then rings of mesenteric artery tissue and bands of trigone were prepared. These rings or strips of tissue were immersed in a modified Krebs solution, oxygenated with a mixture of 95% of 0 2 and 5% of C0 2 . Each tissue sample was subjected to a tension of 1 g and then phenylephrine was added in cumulative doses and the concentration / response curve was established. After rinsing the tissues, the compound to be studied was introduced at cumulative doses and the concentration / response curve established.
- the contractile effect of each compound is evaluated by calculating pD 2 (negative logarithm of the agonist concentration which induces 50% of the maximum contraction) as well as by the maximum effect expressed as a percentage of the contraction obtained with phenylephrine (% Emax) •
- the compounds according to the invention can be used as a drug, in particular as a contracting agent for the smooth muscles of the trigone, and more particularly still, in the treatment of ejaculation troubles such as retrograde ejaculation or aspermia.
- the compounds according to the invention exhibit good efficacy and, usually, less side effects than the drugs conventionally used for such treatment, in particular as regards the side effects affecting the cardiovascular system.
- the compounds according to the invention can be presented in different pharmaceutical forms suitable for administration by the digestive or parenteral route, if necessary by combining with at least one pharmaceutical excipient.
- suitable pharmaceutical forms are for example tablets, capsules, dragees, capsules, oral or injectable solutions, syrups, suppositories.
- These pharmaceutical forms can be dosed to allow a daily dose of 1 ⁇ g / kg to 30 mg / kg.
Landscapes
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU91664/98A AU9166498A (en) | 1997-09-11 | 1998-09-10 | Use of sulphonamide benzene derivatives to obtain a medicine for treating retrograde ejaculation or aspermia |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9711283A FR2768054A1 (fr) | 1997-09-11 | 1997-09-11 | Utilisation de derives de benzene sulfonamide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie |
FR97/11283 | 1997-09-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1999012535A1 true WO1999012535A1 (fr) | 1999-03-18 |
WO1999012535A8 WO1999012535A8 (fr) | 1999-05-27 |
Family
ID=9510966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1998/001927 WO1999012535A1 (fr) | 1997-09-11 | 1998-09-10 | Utilisation de derives de benzene sulfonamide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU9166498A (fr) |
FR (1) | FR2768054A1 (fr) |
WO (1) | WO1999012535A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2463151A (en) * | 2008-09-05 | 2010-03-10 | Acucela Inc | Amine derivative compounds for treating ophthalmic diseases and disorders |
AU2013206281B2 (en) * | 2008-09-05 | 2016-06-02 | Acucela, Inc. | Sulphur-linked compounds for treating ophthalmic diseases and disorders |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6503935B1 (en) | 1998-08-07 | 2003-01-07 | Abbott Laboratories | Imidazoles and related compounds as α1A agonists |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997006136A1 (fr) * | 1995-08-04 | 1997-02-20 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leurs applications en therapeutique |
-
1997
- 1997-09-11 FR FR9711283A patent/FR2768054A1/fr not_active Withdrawn
-
1998
- 1998-09-10 AU AU91664/98A patent/AU9166498A/en not_active Abandoned
- 1998-09-10 WO PCT/FR1998/001927 patent/WO1999012535A1/fr active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997006136A1 (fr) * | 1995-08-04 | 1997-02-20 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leurs applications en therapeutique |
Non-Patent Citations (4)
Title |
---|
DEPLANNE ET AL.: "Functional characterization of alpha-1-adrenoreceptor subtypes in the prostatic urethra and trigone of male rabbit", J. PHARMACOL. EXP. THER., vol. 278, no. 2, August 1996 (1996-08-01), pages 527 - 534, XP002067626 * |
MURAMATSU ET AL.: "Pharmacological profiles of a novel alpha-1-adrenoreceptor agonist, PNO-49B, at alpha-1-adrenoreceptor subtypes", NAUNYN-SCHMIED. ARCH. PHARMACOL., vol. 351, no. 1, January 1995 (1995-01-01), pages 2 - 9, XP002067623 * |
SCHREITER: "Blasenhalsfunktio und Störungen der Sexualfunktionen nach Rektumamputationen bzw. Rektumresektionene und retroperitonealer Lymphadenektomie", ZENTRALBLATT FÜR CHIRURGIE, vol. 99, no. 2, 1974, pages 33 - 40, XP002067625 * |
VAN DER GRAAF ET AL.: "Analysis of alpha1-adrenoreceptors in rabbit lower urinary tract and mesenteric artery", EUR. J. PHARMACOL., vol. 327, no. 1, 26 May 1997 (1997-05-26), pages 25 - 32, XP002067624 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2463151A (en) * | 2008-09-05 | 2010-03-10 | Acucela Inc | Amine derivative compounds for treating ophthalmic diseases and disorders |
AU2013206281B2 (en) * | 2008-09-05 | 2016-06-02 | Acucela, Inc. | Sulphur-linked compounds for treating ophthalmic diseases and disorders |
Also Published As
Publication number | Publication date |
---|---|
AU9166498A (en) | 1999-03-29 |
WO1999012535A8 (fr) | 1999-05-27 |
FR2768054A1 (fr) | 1999-03-12 |
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