WO1994013284A1 - New use of 5-ht3 receptor antagonists - Google Patents
New use of 5-ht3 receptor antagonists Download PDFInfo
- Publication number
- WO1994013284A1 WO1994013284A1 PCT/EP1993/003295 EP9303295W WO9413284A1 WO 1994013284 A1 WO1994013284 A1 WO 1994013284A1 EP 9303295 W EP9303295 W EP 9303295W WO 9413284 A1 WO9413284 A1 WO 9413284A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- treatment
- active ingredient
- oct
- receptor antagonists
- Prior art date
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
Abstract
Use of 5-HT3 receptor antagonists in the treatment of the emesis due to bacterial or viral gastrointestinal infection, or to the enterotoxins released by such microorganisms.
Description
NEW USE OF 5-HT3 RECEPTOR ANTAGONISTS
The present invention relates to a new use of 5- HT3 receptor antagonists in the treatment of emesis due to bacterial or viral gastrointestinal infections or to the enterotoxins released by such microorganisms. Emesis is a complex coordinated reflex which involves different organs and systems, such as the abdominal muscles, the diaphragm, the organs of the upper gastrointestinal tract, the sympathetic and the parasympathetic nervous systems and some structures in the brain. Emesis may be due to different stimuli and it can be initiated either peripherally or centrally. Different classes of pharmacologically active substances are currently employed to treat emesis; such as for example: cholinolytics, antihistamines, dopamine antagonists, centrally acting sympathomimeticε, glucocorticoidε, benzodiazepines, and cannabinoidε [Drugs, 43(3), 295-315 (1992) and ibid. 13(4), 443-463 (1992)]. However, neither a single class of the above substances nor a single substance can be considered as a "general antiemetic" for treating the all different types of emesis. Thus, for example the cholinolytic scopolamine and the antihistaminics are mainly used to treat emesis due to motion sickness. Antihistaminics such as diphenydra ine, promethazine, etc. are also used to treat vomiting due to pregnancy or to vestibular disturbances. Dopamine antagonists, such as metoclopramide and butyrophenones, and phenothiazine are useful to treat chemotherapy and radiation induced emesis, as well as the corticosteroids such as
dexamethasone or methylprednisolone, while domperidon is mainly used to treat emesis due to gastri dysfunctions.
Selective antagonists of serotonergic type receptors (5-HT3 receptor antagonists) were recentl described to possess strong antiemetic efficacy i vomiting induced by chemotherapeutic agents an radiations. Moreover, some of these compounds seem als to be effective in post-operative vomiting. 5~HT3 receptor antagonists may be identified b standard methods, for example using tests in which th antagonism of the Bezold-Jarisch reflex, induced b serotonin in rat as described by Fozard J.B. et al., J. Cardiovasc. Pharmacol 2, 229-245 (1980) is evaluated. Patent Applications EP 309423, EP 351385 (Istituto D Angeli S.p.A.), EP 158265, EP 200444, EP 202062, A 8658939, AU 8660274, EP 212802, EP 214772, EP 220011, EP 221702, US 4816453, EP 230718, AU 8767121, E 235878, EP 239321, EP 254584, EP 255297, EP 261964, E 287196, EP 289170, EP 315316, EP 315390, WO 8909217, A 626614, EP 387431, WO 9101316, WO 9117161, WO 9205174, EP 498466, (Beecham Group p.I.e.), WO 9212149 (Smit Kline Beecham p.l.c), GB 2153821, EP 191562, E 210840, EP 219193, EP 242973, GB 2192885, EP 266899, US4822881, EP 276163, EP 291172, EP 306323, EP 307145, EP 317088, EP 327307, EP 336759, EP 339959, EP 344015, EP 345956, EP 353983, EP 356098, EP 357417, EP 385722, EP 403261, US 5116984 (Glaxo Group Limited), G 2125398, GB 2145416, GB 2152049, GB 2169292, EP 189002, GB 2208862, US 4826838, EP 491664, US 4789673 (Sandoz Limited), EP 297651, EP 322016, EP 338650, EP 350130,
EP 375045, EP 377238, EP 393766, EP 410509, EP 436245 (Duphar International Research B.V.), EP 158532, EP 237281, EP 190920, EP 327335, (A.H. Robins Company, Inc.), AU 619731, US 4657911, EP 311724 (Delalande), EP 67770 (Merrell Tourade Cie), EP 339669, EP 330824, EP 330788, EP 329932, EP 266730 (Merrell Dow Pharm. Inc.), EP 307172, US 4921982, WO 8403281, US 4486441, US 4997956 (Eli Lilly and Company), EP 323077, EP 306148,GB 2208385, EP 361629, GB 2236751, GB 2236528, GB 2213816, GB 2216516, GB 2225574, GB 2247886 (John Wyeth and Brother Limited), US 4290227, US 4857517, US 4859683, EP 339950, US 4920219, US 4924010, US 4935511, WO 9006309, WO 9104738, WO 9116888 (Rorer International Overseas, Inc.), EP 234872, WO 8801866 (Adria Laboratories Inc.), EP 294292, US 5030646 (Adir et Companie), EP 302699 (Fordonal), EP 358903, EP 313393, EP 407137, US 4914207, US 4963689, WO 9107402 (Pfizer), EP 328200, EP 337547, GB 2229182 (Merck, Sharp and Dohme Limited), EP 376624, EP 381422, AU 8716591 (Yamanouchi), EP 378111 (Zambon), EP 403882, EP 420086, EP 392663, EP 405784, EP 482939 (Ono), AU 5650890 (Nippon Shinyaku Co. Limited), US 4992461, EP 454121, US 5137893 (Searle), EP 419397 (Ferrosan), EP 429984, EP 469449 (Nisshin Flour Milling), EP 430190, EP 457243, EP 485962, EP 490263 (Sintex), WO 9112254 (Novo Nordisk), EP 458636, US 5063230, WO 9209284 (Rhone- Poulenc), EP 456519 (Sankyo), EP 483836 (Toyo) describe different classes of 5-HT3 receptor antagonists.
The use of 5-HT3 receptor antagonists in the treatment of emesis induced by administration of chemotherapeutic agents or radiations is claimed in the
A above patent applications, and it has been the subject of different review articles [See for example Drugs 42(4), 551-568 (1991)].
A few compounds such as Ondansetron, Graniεetron and Tropisetron are alεo already marketed for thiε indication, while otherε are in advanced clinical trialε. The usefulness of Ondansetron in the treatment of post-operative vomiting haε alεo been disclosed. 5- HT3 receptor antagonistε have also been claimed for the treatment of vomiting and nausea due to motion sickness.
E esiε due to bacterial or viral gaεtrointestinal infections or to the enterotoxins released by such microorganisms requires an antiemetic treatment especially in the case in which there is an elevated elimination of liquids and electrolytes due to the concomitant diarrhoea. In fact the oral administration of an adequate amount of these substances, in place of those lost, is seriously compromised by vomiting. Currently the treatment of such type of emesis includes the administration of corticosteroids, whereas liquids and electrolytes are intravenouεly adminiεtered.
It haε now been found, and this is the object of the present invention, that 5-HT3 receptor antagoniεts are effective as antiemetic agents in the treatment of emesis due by bacterial or viral gastrointestinal infections or to the enterotoxins released by such microorganismε. Accordingly, the preεent invention provides a method for the treatment of emeεis due to bacterial or
viral gastrointestinal infections or to the enterotoxins released by such microorganisms in mammals, such as humans, which method comprises administering to the mammal in need of such treatment an effective amount of a 5-HT3 receptor antagonist.
Suitable examples of 5-HT receptor antagonists are those discloεed in the aforementioned patent publications. Particular examples of such 5-HT3 receptor antagonists are: DAU 6215, having the chemical name endo-N-(8-methyl-8- azabicyclo[3.2.1]oct-3-yl)2,3-dihydro-2-oxo-lH- benzimidazole-1-carboxamide.
BIMU 1, having the chemical name endo-N-(8-methyl-8- azabicyclo[3.2.1]oct-3-yl)2 ,3-dihydro-3-ethyl-2-oxo-lH- benzimidazole-1-carboxamide.
GR 38032F, also known aε Ondansetron, having the chemical name l,2,3,9-tetrahydro-9-methyl-3-[(2-methyl- lH-imidazol-l-yl)methyl]-4H-carbazol-4-one.
ICS 205930, also known as Tropisetron, having the chemical name endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl indole-3-carboxylate.
BRL 43694, also known aε Granisetron, having the chemical name endo-N-(9-methyl-9-azabicyclo[3.3.1]non- 3-yl)-l-methylimidazole-3-carboxamide. MDL 73147, also known as Dolasetron, having the chemical name trans-hexahγdro-8-(3-indolylcarbonyloxy)- 2,6-methano-2H-quinolizin-3(4H)one.
LY-277359, alεo known aε Zatoεetron, having the chemical name endo-5-chloro-2,3-dihydro-2,2-dimethy1-N- (8-methyl-8-azabicyclo[3.2.l]oct-3-γl)-7-benzofuran carboxamide.
Zacopride, having the chemical name 4-amino-N-[l- azabicyclo(2.2.2)oct-3-γl]-5-chloro-2-methoxy benzamide, most preferably S(-) Zacopride. RG-12915 having the chemical name 4-[N-(l- azabicγclo[2.2.2]octan-3-(5)-γl)]2-chloro-cis 5a-(s)- 9a-(ε)-5a,6,7,8,9,9a-hexahydrobenzofurancarboxamide. ADR-851 having the chemical name 4-amino-5-chloro-N-[2- pyrrolidylmethyl]-2,3-dihγdrobenzo[b]furan-7- carboxamide. ADR-882 having the chemical name 4-amino-N-[l- azabicγclo[2.2.l]oct-3-yl]-5-chloro-2,3- dihydrobenzo[b]furan-7-carboxamide.
YM060 having the chemical name (R)-5-[(l-methyl-3- indolyl)carbonyl]-4,5,6,7-tetrahydro-lH-benzimidazole. Y 25130 having the chemical name (±)-N-(l- azabicyclo[2.2.2]oct-3-yl)-6-chloro-4-methyl-3-oxo-3,4- dihydro-2H-l,4-benzoxazine-8-carboxamide. BRL 46470 having the chemical name endo-N-(8-methyl-8- azabicyclo[3.2.l]oct-3-yl)-2,3-dihydro-3,3-dimethyl indole-1-carboxamide.
GR-68755 having the chemical name 2,3,4,5-tetrahydro-5- methyl-2-[(5-methyl-lH-imidazol-4-yl)methyl]-lH- pyrido[4,3-b]indol-1-one.
The present invention alεo provides the use of a 5-HT3 receptor antagonist for the manufacture of a medicament for the treatment of emeεis due to bacterial or viral gastrointestinal infections, or to the enterotoxins released by such microorganisms.
PHARMACOLOGICAL DATA
Staphylococcal enterotoxin-B-induced e eεiε in the ferret
Male adult ferretε (1 - 1.5 kg b.w. ) were adminiεtered 0.1 mg/kg εtaphylococcal enterotoxin-B intravenously; this treatment induced emesis in 100% of the animals. The antiemetic activity of the compounds was evaluated by administering the substance intravenously 5 min before enterotoxin-B, and scoring the number of the animals protected from vomiting versus the total number of ferretε treated. Under these conditionε the following results were obtained.
According to a further feature of the present invention there are provided pharmaceutical compositions for the treatment of the emesis due to bacterial or viral gastrointestinal infectionε, or to the enterotoxins released by such microorganismε, comprising as active ingredient an effective amount of a 5-HT3 receptor antagonist in asεociation with one or more pharmaceutically acceptable carrierε, diluents or excipients.
The compositions may be formulated in conventional manner, for oral, parenteral, rectal or transder al adminiεtration.
For oral administration, the pharmaceutical compositions may be, for example, in the form of, tablets, (including sustained release tablets) or capsuleε prepared in conventional manner with pharmaceutically acceptable excipients such aε corn εtarch, polyvinylpyrrolidone, lactoεe, microcrystalline cellulose, magnesium εtearate, talc, potato εtarch, εodium lauryl εulphate. Liquid preparationε for oral adminiεtration may be, for example, in the form of εolutionε, εyrupε or εuεpenεionε which may be prepared in conventional manner with pharmaceutically acceptable additives εuch as sorbitol syrup, cellulose derivatives, lecithin, almond oil, methyl p- hydroxybenzoate, and if desired, buffer salts, flavouring, colouring and sweetening agents.
For parenteral administration, the pharmaceutical compoεitions may be, for example, in the form of injection or continuous infusion. The compoεitions for injection may be presented in unit dosage form, e.g. in ampoules or in multi-dose containers. The compositions may be in the form of suspenεionε, solutions or e ulsionε in oily or aqueouε vehicleε. Alternatively, the active ingredient may be in powder form for constitution with a suitable vehicle, e.g. sterile apyrogen water, before use.
For rectal administration the pharmaceutical compositions may be, for example, in the form of suppositories containing conventional suppoεitory baεeε, εuch as cocoa butter or other glycerides. Besideε the above deεcribed compoεitionε, a 5-HT3 receptor antagoniεt may alεo be formulated as depot
compositions. Such long acting compositions may be administered by implantation (for example subcutaneously, transcutaneously or intramuεcularly) or by intramuεcular injection. Thuε, these preparations may be, for example, formulated with suitable polymeric or hydrophobic materials or ion exchange resinε.
The compoεitonε are advantageouεly formulated in dosage unit; each dosage unit being adapted to supply a single dose of the active ingredient. Each dosage unit may conveniently contain from 0.001 mg to 300 mg, preferable from 0.1 mg to 100 mg of the active ingredient.
The following examples describe the incorporation of the 5-HT receptor antagonist into the conventional pharmaceutical compositionε for use according to the invention and should not be intended as limiting the invention thereto. EXAMPLE 1 Tablets - Active ingredient 0.50 mg lactose spray dried 67.25 " microcrystalline cellulose 21.80 " magnesium stearate BP 0.45 "
Tablet weight 90.00 mg
Method of preparation: the active ingredient was passed through a 24/cm mesh sieve, blended with the lactose, microcrystalline celluloεe and magneεium stearate. The reεulting mixture was presεed into tablets weight 90 mg each. Each tablet contains 0.50 g of
active ingredient.
EXAMPLE 2
Capsules active ingredient 0.50 mg lactoεe 98.50 " magnesium εtearate BP 1.00 "
Fill Weight 100.00 mg
Method of preparation: the active ingredient was sieved and blended with the excipients. The mixture was filled into hard gelatin capsules using suitable machinary. EXAMPLE 3 Syrup - active ingredient 0.50 mg hydroxypropylmethylcellulose USP 22.50 " Buffer
water, cooled and then mixed with an aqueous solution containing the active ingredient and the other components of formulation. The resultant solution was adjuεted to volume and mixed. The syrup was clarified by filtration.
EXAMPLE 4 Ampoules active ingredient 0.05 mg 0.5 mg sodium chloride BP as required aε required - water for injection BP to 1.0 ml 1.0 ml
Sodium chloride may be added to adjust the tonicity of the εolution and the pH may be adjuεted, using acid or alkali, to that of optimum stability and/or facilitate solution of the active ingredient. Alternatively suitable buffer salts may be used.
Method of preparation: the solution was prepared, clarified and filled into appropriate size ampoules sealed by fusion of the glass. The ampoule was sterilised by heating in an autoclave using one of the acceptable cycles. Alternatively the solution may be sterilised by filtration and filled into sterile ampoules under aseptic conditions. The solution may be packed under an inert atmoεphere of nitrogen or other suitable gas. EXAMPLE 5
Supposi tori es active ingredient 0.50 mg witepsol H35 to 1.0 g
Method of preparation: a suspension of the active ingredient was prepared in the molten witepεol and filled, uεing εuitable machinary, into εuppoεitory moulds.
Claims
1. Use of a 5-HT3 receptor antagonist for the manufacture of a medicament for the treatment of the emesiε due to bacterial or viral gastrointestinal infections, or to the enterotoxins released by such microorganisms.
2. Use according to claim 1 in which the 5-HT3 receptor antagonist is selected from endo-N-(8-methyl-8-azabicyclo[3.2.1. ]oct-3-yl)2,3- dihydro-2-oxo-lH-benzimidazole-l-carboxamide;
1,2,3,9-tetrahydro-9-methγl-3-[(2-methyl-lH-imidazol-l- yl)methyl]-4H-carbazol-4-one; endo-8-methyl-8-azabicγclo[3.2.1]oct-3-yl indole-3-car- boxylate.
3. Pharmaceutical compositions for the treatment of the emesiε due to bacterial or viral gastrointestinal infections, or to the enterotoxims released by εuch microorganiεms, containing as active ingredient an effective amount of a 5-HT3 receptor antagoniεt together with pharmacologically acceptable carriers or excipients.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU56271/94A AU5627194A (en) | 1992-12-15 | 1993-11-24 | New use of 5-ht3 receptor antagonists |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT002854A ITMI922854A1 (en) | 1992-12-15 | 1992-12-15 | USE OF 5-HT3 RECEPTOR ANTAGONISTS |
ITMI92A002854 | 1992-12-15 |
Publications (1)
Publication Number | Publication Date |
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WO1994013284A1 true WO1994013284A1 (en) | 1994-06-23 |
Family
ID=11364461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1993/003295 WO1994013284A1 (en) | 1992-12-15 | 1993-11-24 | New use of 5-ht3 receptor antagonists |
Country Status (3)
Country | Link |
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AU (1) | AU5627194A (en) |
IT (1) | ITMI922854A1 (en) |
WO (1) | WO1994013284A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727015A1 (en) * | 1994-11-22 | 1996-05-24 | Glaxo Wellcome Inc | ONDANSETRON LIQUID PHARMACEUTICAL COMPOSITIONS |
US9021538B2 (en) | 1998-07-14 | 2015-04-28 | Rovi Guides, Inc. | Client-server based interactive guide with server recording |
US9071872B2 (en) | 2003-01-30 | 2015-06-30 | Rovi Guides, Inc. | Interactive television systems with digital video recording and adjustable reminders |
US9125169B2 (en) | 2011-12-23 | 2015-09-01 | Rovi Guides, Inc. | Methods and systems for performing actions based on location-based rules |
US9294799B2 (en) | 2000-10-11 | 2016-03-22 | Rovi Guides, Inc. | Systems and methods for providing storage of data on servers in an on-demand media delivery system |
US9326025B2 (en) | 2007-03-09 | 2016-04-26 | Rovi Technologies Corporation | Media content search results ranked by popularity |
US10063934B2 (en) | 2008-11-25 | 2018-08-28 | Rovi Technologies Corporation | Reducing unicast session duration with restart TV |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021673A1 (en) * | 1991-05-28 | 1992-12-10 | Syntex (U.S.A.) Inc. | Novel azabicyclobenzisoquinolines |
-
1992
- 1992-12-15 IT IT002854A patent/ITMI922854A1/en unknown
-
1993
- 1993-11-24 AU AU56271/94A patent/AU5627194A/en not_active Abandoned
- 1993-11-24 WO PCT/EP1993/003295 patent/WO1994013284A1/en active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021673A1 (en) * | 1991-05-28 | 1992-12-10 | Syntex (U.S.A.) Inc. | Novel azabicyclobenzisoquinolines |
Non-Patent Citations (5)
Title |
---|
"Upjohn/Boeringer Ingelheim central nervous system (CNS) agreement", SCRIP, vol. 1775, 1 December 1992 (1992-12-01), pages 13 * |
Dialog Information Sevices File 129: Pharmaceutical and Healthcare IndustryNews Database 1980-1994 Accession No. 343484 * |
E. BEUBLER ET AL.: "5-HT receptor antagonists and heat-stable Escherichia coli enterotoxin-induced effects in the rat", EUR. J. PHARMACOL., vol. 219, no. 3, 4 September 1992 (1992-09-04), pages 445 - 450 * |
F. MITCHELSON: "Pharmacological agents affecting emesis", DRUGS, vol. 43, no. 3, 1992, pages 295 - 315 * |
J. FIORAMONTI ET AL.: "Delayed gastric emptying induced in mice by the mycotoxin deoxynivalenol is reversed by the 5HT3 receptor antagonists", GASTROENTEROLOGY, vol. 102, no. 4-P2, 1992, pages A448 * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727015A1 (en) * | 1994-11-22 | 1996-05-24 | Glaxo Wellcome Inc | ONDANSETRON LIQUID PHARMACEUTICAL COMPOSITIONS |
WO1996015786A2 (en) * | 1994-11-22 | 1996-05-30 | Glaxo Wellcome Inc. | Oral compositions containing ondansetron |
WO1996015786A3 (en) * | 1994-11-22 | 1996-06-27 | Glaxo Wellcome Inc | Oral compositions containing ondansetron |
BE1009458A5 (en) * | 1994-11-22 | 1997-04-01 | Glaxo Wellcome Inc | Pharmaceutical oral liquid containing imidazolecarbazolone. |
US5854270A (en) * | 1994-11-22 | 1998-12-29 | Glaxo Wellcome Inc. | Oral compositions containing ondansetron |
US9226006B2 (en) | 1998-07-14 | 2015-12-29 | Rovi Guides, Inc. | Client-server based interactive guide with server recording |
US9055318B2 (en) | 1998-07-14 | 2015-06-09 | Rovi Guides, Inc. | Client-server based interactive guide with server storage |
US9055319B2 (en) | 1998-07-14 | 2015-06-09 | Rovi Guides, Inc. | Interactive guide with recording |
US9118948B2 (en) | 1998-07-14 | 2015-08-25 | Rovi Guides, Inc. | Client-server based interactive guide with server recording |
US10075746B2 (en) | 1998-07-14 | 2018-09-11 | Rovi Guides, Inc. | Client-server based interactive television guide with server recording |
US9154843B2 (en) | 1998-07-14 | 2015-10-06 | Rovi Guides, Inc. | Client-server based interactive guide with server recording |
US9232254B2 (en) | 1998-07-14 | 2016-01-05 | Rovi Guides, Inc. | Client-server based interactive television guide with server recording |
US9021538B2 (en) | 1998-07-14 | 2015-04-28 | Rovi Guides, Inc. | Client-server based interactive guide with server recording |
US9294799B2 (en) | 2000-10-11 | 2016-03-22 | Rovi Guides, Inc. | Systems and methods for providing storage of data on servers in an on-demand media delivery system |
US9071872B2 (en) | 2003-01-30 | 2015-06-30 | Rovi Guides, Inc. | Interactive television systems with digital video recording and adjustable reminders |
US9369741B2 (en) | 2003-01-30 | 2016-06-14 | Rovi Guides, Inc. | Interactive television systems with digital video recording and adjustable reminders |
US9326025B2 (en) | 2007-03-09 | 2016-04-26 | Rovi Technologies Corporation | Media content search results ranked by popularity |
US10694256B2 (en) | 2007-03-09 | 2020-06-23 | Rovi Technologies Corporation | Media content search results ranked by popularity |
US10063934B2 (en) | 2008-11-25 | 2018-08-28 | Rovi Technologies Corporation | Reducing unicast session duration with restart TV |
US9125169B2 (en) | 2011-12-23 | 2015-09-01 | Rovi Guides, Inc. | Methods and systems for performing actions based on location-based rules |
Also Published As
Publication number | Publication date |
---|---|
AU5627194A (en) | 1994-07-04 |
ITMI922854A0 (en) | 1992-12-14 |
ITMI922854A1 (en) | 1994-06-15 |
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