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WO1996033723A2 - Utilisation de derives benzamides pour traiter et/ou prevenir le syndrome de meniere et le mal des transports - Google Patents

Utilisation de derives benzamides pour traiter et/ou prevenir le syndrome de meniere et le mal des transports Download PDF

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Publication number
WO1996033723A2
WO1996033723A2 PCT/JP1996/001112 JP9601112W WO9633723A2 WO 1996033723 A2 WO1996033723 A2 WO 1996033723A2 JP 9601112 W JP9601112 W JP 9601112W WO 9633723 A2 WO9633723 A2 WO 9633723A2
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
meniere
syndrome
acyl
Prior art date
Application number
PCT/JP1996/001112
Other languages
English (en)
Other versions
WO1996033723A3 (fr
Inventor
Masayuki Ishie
Original Assignee
Fujisawa Pharmaceutical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fujisawa Pharmaceutical Co., Ltd. filed Critical Fujisawa Pharmaceutical Co., Ltd.
Priority to JP8524148A priority Critical patent/JPH11503721A/ja
Publication of WO1996033723A2 publication Critical patent/WO1996033723A2/fr
Publication of WO1996033723A3 publication Critical patent/WO1996033723A3/fr

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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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep

Definitions

  • This invention relates to a new use of benzamide
  • benzamide derivatives used in this invention are known as described in European Patent Application Publication No. 0 620 216 that said benzamide derivatives possess activities as vasopressin antagonistic activity, vasodilating activity, hypotensive activity, activity for inhibiting growth of
  • mesangium cells water diuretic activity, platelet agglutination inhibitory activity or oxytocin antagonistic activity and are useful in the treatment and/or prevention of hypertension, heart failure, renal insufficiency, edema, ascites, vasopressin parasecretion syndrome, hepatocirrhosis, hyponatremia,
  • This invention relates to a new use of benzamide
  • liver activity for inhibiting growth of mesangium cells, water diuretic activity, platelet agglutination inhibitory activity or oxytocin antagonistic activity, for treating and/or preventing Meniere's syndrome (e.g. Meniere's disease, etc.) or motion sickness.
  • Meniere's syndrome e.g. Meniere's disease, etc.
  • this invention provides a new use of benzamide derivatives for treating and/or preventing
  • Meniere's syndrome e.g. Meniere's disease, etc.
  • motion sickness e.g. Meniere's syndrome, etc.
  • this invention provides an agent and a
  • Meniere's syndrome e.g. Meniere's disease, etc.
  • motion sickness which comprises said benzamide derivatives.
  • this invention provides a method for treating and/or preventing Meniere's syndrome (e.g. Meniere's disease, etc.) or motion sickness, which comprises
  • the benzamide derivatives used in this invention can be represented by the following general formula (I).
  • R 1 is hydrogen or lower alkyl
  • R 2 is hydrogen, lower alkyl, halo (lower) alkyl, halogen or lower alkoxy,
  • R 3 and R 4 are each hydrogen, lower alkyl or taken
  • R 5 is hydrogen, halogen, nitro, hydroxy, protected
  • R 6 is hydrogen, lowing alkyl or acyl
  • A is K in which
  • R 7 is hydrogen; lower alkyl optionally substituted with halogen, amino, lower alkylamino, protected amino, acyl, a heterocyclic group, hydroxy or
  • R 8 and R 9 are each hydrogen, or taken together to form oxo or thioxo; or
  • R 7 and R 8 are taken together to form a bond
  • R 9 is lower alkylamino, N-lower
  • alkylpiperazinyl or lower alkylthio optionally substituted with lower alkylamino
  • R 10 is hydrogen
  • R 11 is hydrogen, hydroxy, lower alkylamino or lower alkyl optionally substituted with acyl; or
  • R 10 and R 11 are taken together to form oxo or lower alkoxyimino optionally substituted with acyl;
  • R 12 is lower alkyl optionally substituted with acyl
  • R 13 is lower alkyl
  • X 1 is CH or N
  • X 2 is CH or N, in which
  • R 14 is hydrogen, halogen, hydroxy or lower alkoxy
  • R 15 is aryloxy, naphthyl, phenyl substituted with substituent (s) selected from the group consisting of lower alkyl, lower alkoxy, halogen, halo (lower) alkyl, hydroxy, amino (lower) alkyl,
  • R 16 is aryl
  • n 0, 1, 2 or 3
  • Said compound (I) and pharmaceutically acceptable salts thereof are useful in the treatment and/or prevention of Meniere's syndrome (e.g. Meniere's disease, etc.) or motion sickness in mammals.
  • lower is intended to mean a group having 1 to 6 carbon atom (s), preferably one having 1 to 4 carbon
  • lower alkyl and lower alkyl moiety in the terms "halo (lower) alkyl", “amino (lower) alkyl”, “N-lower alkylpiperazinyl”, “lower alkylthio”, “N-lower alkyl- piperazinylcarbonyl", “lower alkylsulfonyl”,
  • acylamino (lower) alkyl may be straight or branched one such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl or the like, in which preferable one is C 1 -C 4 alkyl such as methyl, ethyl, propyl, isobutyl or tert-butyl.
  • Suitable "aryl” and aryl moiety in the terms “aryloxy” and “arylsulfonyl” may be phenyl, naphthyl, phenyl
  • lower alkyl e.g. tolyl, xylyl, mesityl, cumenyl, di (tert-butyl) pentyl, etc.
  • preferable one is phenyl or tolyl.
  • Suitable "halogen” may be fluorine, chlorine, bromine and iodine, in which preferable one is fluorine or chlorine.
  • Suitable "lower alkoxy” and lower alkoxy moiety in the term “lower alkoxyimino” may be methoxy, ethoxy, propoxy, isopropoxy, butoxy and the like, in which preferable one is methoxy or propoxy.
  • Suitable "lower alkylamino” may be mono or di (lower alkyl) amino such as methylamino, ethylamino, propylamino, isopropylamino, butylamino, tert-butylamino, isobutylamino, pentylamino, hexylamino, dimethylamino, diethylamino,
  • preferable one is dimethylamino.
  • Suitable “lower alkylamino (lower) alkyl” may be mono or di (lower alkyl) amino substituted lower alkyl such as
  • methylaminomethyl methylaminoethyl, methylaminopropyl, methylaminobutyl, methylaminohexyl, ethylaminomethyl,
  • ethylaminohexyl dimethylaminomethyl, dimethylaminoethyl, dimethylaminopropyl, dimethylaminobutyl, dimethylaminohexyl, diethylaminomethyl, diethylaminoethyl, diethylaminopropyl, diethylaminobutyl, diethylaminohexyl or the like, in which preferable one is dimethylaminoethyl, dimethylaminopropyl or dimethylaminobutyl.
  • Suitable "halo (lower) alkyl” may be chloromethyl, fluoromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl and the like, in which preferable one is trifluoromethyl.
  • heterocyclic group and a heterocyclic moiety in the terms "a heterocyclic (lower) alkyl” and "a
  • heterocycliccarbonyl may be one containing at least one hetero atom selected from nitrogen, sulfur and oxygen atom, and may include saturated or unsaturated, monocyclic or polycyclic heterocyclic group, and preferable heterocyclic group may be N-containing heterocyclic group such as
  • unsaturated 3 to 6-membered heteromonocyclic group containing 1 to 4 nitrogen atoms for example, pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazolyl [e.g. 4H-1,2,4-triazolyl, 1H-1,2,3- triazolyl, 2H-1,2,3-triazolyl, etc.], tetrazolyl [e.g. 1H- tetrazolyl, 2H-tetrazolyl, etc.], etc.;
  • unsaturated condensed heterocyclic group containing 1 to 5 nitrogen atoms for example, indolyl, isoindolyl,
  • unsaturated 3 to 6-membered heteromonocyclic group containing an oxygen atom for example, pyranyl, furyl, etc.;
  • oxazolyl isoxazolyl
  • oxadiazolyl e.g. 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, etc.
  • unsaturated condensed heterocyclic group containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms e.g. benzofurazanyl, benzoxazolyl, benzoxadiazolyl, etc.];
  • unsaturated 3 to 6-membered heteromonocyclic group containing 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms for example, thiazolyl, thiadiazolyl [e.g., 1,2,4-thiadiazolyl, 1,3,4- thiadiazolyl, 1,2,5-thiadiazolyl, etc.], etc.;
  • unsaturated condensed heterocyclic group containing 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms e.g., benzothiazolyl, benzothiadiazolyl, etc.
  • unsaturated condensed heterocyclic group containing 1 to 2 oxygen atoms e.g. benzofuranyl, benzodioxolyl, etc.
  • unsaturated condensed heterocyclic group containing 1 to 2 oxygen atoms e.g. benzofuranyl, benzodioxolyl, etc.
  • heterocyclic group may be substituted with lower alkyl optionally substituted with hydroxy, acyloxy, amino, protected amino, acyl, aryl or methylenedioxyphenyl; acyl or a heterocyclic group, in which preferable one is piperazinyl, N-methylpiperazinyl, N,N-dimethylpiperazinyl,
  • N-tert-butoxycarbonylpiperazinyl N-pyridylpiperazinyl, dimethylaminopiperidyl, pyrrolyl, pyridyl, piperidyl, morpholinyl or quinuclidinyl.
  • acylamino (lower) alkyl and “acyl (lower) alkyl” may be
  • alkylsulfonyl alkylsulfonyl, arylsulfonyl and the like.
  • the esterified carboxy may be substituted or
  • unsubstituted lower alkoxycarbonyl e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,
  • aryloxycarbonyl e.g. phenoxycarbonyl
  • substituted or unsubstituted ar (lower) alkoxycarbonyl e.g. benzyloxycarbonyl, phenethyloxycarbonyl,
  • the lower alkylcarbamoyl may be mono or
  • di (lower) alkylcarbamoyl such as methylcarbamoyl
  • the lower alkanoyl may be substituted or unsubstituted one such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, trifluoroacetyl or the like, in which preferable one is formyl or acetyl.
  • the aroyl may be substituted or unsubstituted one such as benzoyl, naphthoyl, toluoyl, di (tert-butyl) benzoyl,
  • the lower alkylsulfonyl may be methylsulfonyl
  • the arylsulfonyl may be substituted or unsubstituted one such as phenylsulfonyl, tolylsulfonyl,
  • N-Protective group in “protected amino” may be common N-protective group such as substituted or unsubstituted lower alkanoyl [e.g. formyl, acetyl, propionyl, trifluoroacetyl, etc.], phthaloyl, lower alkoxycarbonyl [e.g.
  • nitrophenylsulfenyl aralkyl [e.g. trityl, benzyl, etc.] or the like, in which preferable one is phthaloyl or tert- butoxycarbonyl.
  • Protected hydroxy may be commonly protected hydroxy such as substituted lower alkoxy such as lower
  • alkoxy (lower) alkoxy [e.g. methoxymethoxy, etc.]
  • propionyloxy, pivaloyloxy, etc.] aroyloxy [e.g. benzoyloxy, fluorenecarbonyloxy, etc.], lower alkoxycarbonyloxy [e.g.
  • the phenyl group for R 15 may be substituted with 1 to 5 substituent (s) as mentioned above, wherein the preferable number of the substituent (s) is 1 to 2.
  • Preferable compound (I) is one which has hydrogen for R 1 , hydrogen, lower alkyl or halogen for R 2 , hydrogen for R 3 , hydrogen for R 4 , hydrogen or lower alkoxy for R 5 , hydrogen for R 6 , (wherein R 7 is lower alkyl
  • R 11 is hydrogen, lower alkylamino or acyl (lower) alkyl) for
  • More preferable compound (I) is one which has hydrogen for R 1 , hydrogen, lower alkyl or halogen for R 2 , hydrogen for R 3 , hydrogen for R 4 , hydrogen or lower alkoxy for R 5 , hydrogen for R 6 , - (wherein R 7 is lower alkyl
  • alkylpiperazinylcarbonyl for A, CH for X 1 , CH for X 2 , (wherein R 15 is phenyl substituted with lower alkyl or di (lower alkyl)) for Y, and 0, 1 or 2 for n.
  • compound (I) is 5- ⁇ 4-[2-(4- methylphenyl)benzoylamino]benzoyl ⁇ -1-[(4-methyl-1- piperazinyl)carbonylmethyl]-1,3,4,5-tetrahydro-1,5- benzodiazepin-2(2H)-one.
  • Suitable pharmaceutically acceptable salts of the compound (I) are conventional non-toxic salts and include an acid addition salt such as an inorganic acid addition salt [e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.], an organic acid addition salt [e.g. formate, acetate,
  • a metal salt such as an alkali metal salt [e.g. sodium salt, potassium salt, etc.] and an alkaline earth metal salt [e.g. calcium salt, magnesium salt, etc.] and the like.
  • the compound (I) may include one or more stereoisomer (s) such as optical isomer(s) and
  • Guinea-pigs were anesthetized with sodium pentobarbital (30mg/kg, i.p.). After tracheotomy, animals were maintained under artificial respiration. The cochlea was exposed using a ventrolateral approach. Endocochlear potential (EP) was recorded by means of a glass microelectrode inserted into the scala media. The Ag/AgCl reference electrode was placed on the exposed neck muscle.
  • EP Endocochlear potential
  • Arginine vasopressin (AVP) and the test compound were dissolved in saline. AVP (10 -5 M), the test compound
  • the compound (I) of this invention has an inhibitory activity against a negative deflection of endocochlear potential induced by arginine vasopressin and is useful for treating and/or preventing Meniere's syndrome (e.g. Meniere's disease, etc.) or motion sickness.
  • pharmaceutically acceptable salts thereof of the present invention can be used in a form of pharmaceutical preparation containing one of said compounds, as an active ingredient, in admixture with a pharmaceutically acceptable carrier such as an organic or inorganic solid or liquid excipient suitable for oral, parenteral or external (topical) administration.
  • a pharmaceutically acceptable carrier such as an organic or inorganic solid or liquid excipient suitable for oral, parenteral or external (topical) administration.
  • the pharmaceutical preparations may be capsules, tablets, dragees, granules, solution, suspension, emulsion, ointment, or the like. If desired, there may be included in these preparations, auxiliary substances, stabilizing agents, wetting or emulsifying agents, buffers and other commonly used additives.
  • an average single dose of about 0.1 mg, 1 mg, 10 mg, 50 mg, 100 mg, 250 mg, 500 mg and 1000 mg of the compound (I) may be effective for treating and/or preventing Meniere's syndrome (e.g. Meniere's disease, etc.) or motion sickness.
  • Meniere's syndrome e.g. Meniere's disease, etc.
  • motion sickness e.g. motion sickness, etc.
  • amounts between 0.1 mg/body and about 1,000 mg/body may be administered per day.

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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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Utilisation d'un composé de la formule (I), dans laquelle chaque symbole est tel que défini dans la description, ou du sel pharmaceutiquement acceptable de ce composé, pour le traitement et/ou la prévention du syndrome de Ménière ou du mal des transports.
PCT/JP1996/001112 1995-04-28 1996-04-24 Utilisation de derives benzamides pour traiter et/ou prevenir le syndrome de meniere et le mal des transports WO1996033723A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP8524148A JPH11503721A (ja) 1995-04-28 1996-04-24 ベンズアミド誘導体の新規用途

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9508637.7A GB9508637D0 (en) 1995-04-28 1995-04-28 New use
GB9508637.7 1995-04-28

Publications (2)

Publication Number Publication Date
WO1996033723A2 true WO1996033723A2 (fr) 1996-10-31
WO1996033723A3 WO1996033723A3 (fr) 1997-01-30

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GB (1) GB9508637D0 (fr)
WO (1) WO1996033723A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7351709B2 (en) 2004-06-09 2008-04-01 Wyeth Estrogen receptor ligands
US9096546B2 (en) 2007-05-10 2015-08-04 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
US9241942B2 (en) 2007-06-08 2016-01-26 Mannkind Corporation IRE-1α inhibitors
US9422281B2 (en) 2013-11-18 2016-08-23 Forma Therapeutics, Inc. Benzopiperazine compositions as BET bromodomain inhibitors
US10336722B2 (en) 2013-11-18 2019-07-02 Forma Therapeutics, Inc. Tetrahydroquinoline compositions as BET bromodomain inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9307527D0 (en) * 1993-04-13 1993-06-02 Fujisawa Pharmaceutical Co New venzamide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7351709B2 (en) 2004-06-09 2008-04-01 Wyeth Estrogen receptor ligands
US9096546B2 (en) 2007-05-10 2015-08-04 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
US9241942B2 (en) 2007-06-08 2016-01-26 Mannkind Corporation IRE-1α inhibitors
US9546149B2 (en) 2007-06-08 2017-01-17 Mannkind Corporation IRE-1α inhibitors
US9981901B2 (en) 2007-06-08 2018-05-29 Fosun Orinove Pharmatech, Inc. IRE-1α inhibitors
US9422281B2 (en) 2013-11-18 2016-08-23 Forma Therapeutics, Inc. Benzopiperazine compositions as BET bromodomain inhibitors
US10336722B2 (en) 2013-11-18 2019-07-02 Forma Therapeutics, Inc. Tetrahydroquinoline compositions as BET bromodomain inhibitors
US10377769B2 (en) 2013-11-18 2019-08-13 Forma Therapeutics, Inc. Benzopiperazine compositions as BET bromodomain inhibitors
US10611750B2 (en) 2013-11-18 2020-04-07 Forma Therapeutics, Inc. Tetrahydroquinoline compositions as bet bromodomain inhibitors
US10703764B2 (en) 2013-11-18 2020-07-07 Forma Therapeutics, Inc. Benzopiperazine compositions as BET bromodomain inhibitors
US11084831B1 (en) 2013-11-18 2021-08-10 Forma Therapeutics, Inc. Benzopiperazine compositions as BET bromodomain inhibitors
US11111229B2 (en) 2013-11-18 2021-09-07 Forma Therapeutics, Inc. Tetrahydroquinoline compositions as BET bromodomain inhibitors

Also Published As

Publication number Publication date
WO1996033723A3 (fr) 1997-01-30
JPH11503721A (ja) 1999-03-30
GB9508637D0 (en) 1995-06-14

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