WO2007048803A1 - Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders - Google Patents

Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders Download PDF

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Publication number
WO2007048803A1
WO2007048803A1 PCT/EP2006/067757 EP2006067757W WO2007048803A1 WO 2007048803 A1 WO2007048803 A1 WO 2007048803A1 EP 2006067757 W EP2006067757 W EP 2006067757W WO 2007048803 A1 WO2007048803 A1 WO 2007048803A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
use according
premenstrual
treatment
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.)
Ceased
Application number
PCT/EP2006/067757
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English (en)
French (fr)
Inventor
Angelo Ceci
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
Original Assignee
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
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 Boehringer Ingelheim International GmbH, Boehringer Ingelheim Pharma GmbH and Co KG, Boehringer Ingelheim Pharmaceuticals Inc filed Critical Boehringer Ingelheim International GmbH
Priority to CA2626134A priority Critical patent/CA2626134C/en
Priority to JP2008537094A priority patent/JP2009513604A/ja
Priority to US12/091,848 priority patent/US7923449B2/en
Priority to EP06807537A priority patent/EP1945214A1/en
Publication of WO2007048803A1 publication Critical patent/WO2007048803A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the invention relates to the use of benzimidazolone derivatives of formula (I) and their acid addition salts for the preparation of a medicament for the treatment of premenstrual and other female sexual disorders.
  • R 1 , R 2 , R3, and R 4 denote hydrogen or hydroxy with the proviso that R 1 , R 2 , R 3 , and R 4 cannot simultaneously represent hydrogen.
  • Preferred compounds according to the present invention are those of general formula (I) wherein two or three of the four radicals R 1 , R 2 , R3, and R 4 denote hydrogen.
  • ⁇ disorders include depression, schizophrenia, Parkinson, anxiety, sleep disturbances, sexual and mental disorders and age associated memory impairment (WO 01/21593 A1 ).
  • the generic term "Sexual disorders” includes sexual Desire Disorders, sexual Arousal Disorders, Orgasmic Disorders, sexual Pain Disorders, sexual Dysfunction due to a General Medical Condition, Substance-Induced Sexual Dysfunction, and Sexual Dysfunction not otherwise specified (Diagnostic and Statistical Manual of Mental Disorders, 4th edition, Text Revision. Washington DC, American Psychiatric Association, 2000).
  • the present invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of premenstrual disorders.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of
  • the invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of premenstrual disorders selected from the group consisting of premenstrual dysphoria, premenstrual syndrome, premenstrual dysphoric disorder.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of premenstrual disorders selected from the group consisting of premenstrual dysphoria, premenstrual syndrome, premenstrual dysphoric disorder.
  • premenstrual disorders selected from the group consisting of premenstrual dysphoria, premenstrual syndrome, premenstrual dysphoric disorder.
  • the invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of sexual arousal disorder in females.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of sexual arousal disorder in females.
  • the invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of orgasmic disorder in females.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of orgasmic disorder in females.
  • the invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of sexual pain disorders in females.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment of sexual pain disorders in females.
  • the invention relates to the use of the compounds of formula (I), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment sexual pain disorders selected from the group consisting of dyspareunia, vaginismus, noncoital sexual pain disorder, sexual dysfunction due to a general medical condition and substance-induced sexual dysfunction.
  • the present invention relates to the use of the compounds of formula (I) selected from the group consisting of the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally in form of the pharmacologically acceptable acid addition salts thereof for the preparation of a medicament for the treatment sexual pain disorders selected from the group consisting of dyspareunia, vaginismus, noncoital sexual pain disorder, sexual dysfunction due to a general medical condition and substance-induced sexual dysfunction.
  • sexual pain disorders selected from the group consisting of dyspareunia, vaginismus, noncoital sexual pain disorder, sexual dysfunction due to a general medical condition and substance-induced sexual dysfunction.
  • the term "lifelong” refers to such sexual disorders of the present invention, which have been present since the onset of sexual functioning.
  • the term “acquired” refers to such sexual disorders of the present invention which developed only after a period of normal sexual functioning.
  • the ..generalized type refers to such sexual disorders of the present invention wherein the disorder is not limited to certain types of stimulation, situations, or partners.
  • the ..situational type applies to such sexual disorders of the present invention wherein the disorder is limited to certain types of stimulation, situations, or partners.
  • “psychological factors” applies when psychological factors are judged to have the major role in the onset, severity, exacerbation, or maintenance of the sexual disorder, and general medical conditions and substance play no role in the etiology of the sexual disorder. Finally the subtype due to “combined factors” applies when 1 ) psychological factors are judged to have a role in the onset, severity, exacerbation, or maintenance of the sexual disorder, and 2) a general medical condition or substance use is also judged to be contributory but is not sufficient to account for a sexual disorder (Diagnostic and Statistical Manual of Mental Disorders, 4th edition, Text Revision. Washington DC, American Psychiatric Association, 2000).
  • the compounds of formula (I) and the the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h) can be used either as free base or in form of its pharmaceutically acceptable acid addition salts.
  • ..acceptable acid addition salts includes both organic and inorganic acids such as maleic, citric, tartaric, methanesulphonic, acetic, benzoic, succinic, gluconic, isethionic, glycinic, lactic, malic, mucoic, glutamic, sulphamic and ascorbic acid; inorganic acids include hydrochloric, hydrobromic, nitric, sulfuric, or phosphoric acid, and mixtures thereof.
  • organic and inorganic acids such as maleic, citric, tartaric, methanesulphonic, acetic, benzoic, succinic, gluconic, isethionic, glycinic, lactic, malic, mucoic, glutamic, sulphamic and ascorbic acid
  • inorganic acids include hydrochloric, hydrobromic, nitric, sulfuric, or phosphoric acid, and mixtures thereof.
  • the compounds of formula (I) and the compounds (I. a), (l.b), (l.c), (l.d), (l.e), (l.f), (l.g) and (l.h), optionally used in form of its pharmaceutically acceptable acid addition salts, may be incorporated into the conventional pharmaceutical preparation in solid, liquid or spray form.
  • the composition may, for example, be presented in a form suitable for oral, rectal, parenteral administration or for nasal inhalation: preferred forms includes for example, capsules, tablets, coated tablets, ampoules, suppositories and nasal spray.
  • the active ingredient may be incorporated in excipients or carriers conventionally used in pharmaceutical compositions such as, for example, talc, arabic gum, lactose, gelatine, magnesium stearate, corn starch, acqueous or non acqueous vehicles, polyvynil pyrrolidone, semisynthetic glicerides of fatty acids, benzalconium chloride, sodium phosphate, EDTA, polysorbate 80.
  • the compositions are advantageously formulated in dosage units, each dosage unit being adapted to supply a single dose of the active ingredient.
  • the dosis range applicable per day is between 0.1 to 400, preferably between 1.0 to 300, more preferably between 2 to 200 mg.
  • Each dosage unit may conveniently contain from 0,01 mg to 100 mg, preferably from 0,1 to 50 mg.
  • Suitable tablets may be obtained, for example, by mixing the active substance(s) with known excipients, for example inert diluents such as calcium carbonate, calcium phosphate or lactose, disintegrants such as corn starch or alginic acid, binders such as starch or gelatine, lubricants such as magnesium stearate or talc and/or agents for delaying release, such as carboxymethyl cellulose, cellulose acetate phthalate, or polyvinyl acetate.
  • excipients for example inert diluents such as calcium carbonate, calcium phosphate or lactose, disintegrants such as corn starch or alginic acid, binders such as starch or gelatine, lubricants such as magnesium stearate or talc and/or agents for delaying release, such as carboxymethyl cellulose, cellulose acetate phthalate, or polyvinyl acetate.
  • excipients for example inert dilu
  • Coated tablets may be prepared accordingly by coating cores produced analogously to the tablets with substances normally used for tablet coatings, for example collidone or shellac, gum arabic, talc, titanium dioxide or sugar.
  • the core may also consist of a number of layers.
  • the tablet coating may consist of a number or layers to achieve delayed release, possibly using the excipients mentioned above for the tablets.
  • Solutions for injection are prepared in the usual way, e.g of. with the addition of preservatives such as p-hydroxybenzoates, or stabilisers such as alkali metal salts of ethylenediamine tetraacetic acid, and transferred into injection vials or ampoules.
  • preservatives such as p-hydroxybenzoates, or stabilisers such as alkali metal salts of ethylenediamine tetraacetic acid
  • Capsules containing one or more active substances or combinations of active substances may for example be prepared by mixing the active substances with inert carriers such as lactose or sorbitol and packing them into gelatine capsules.
  • Suitable suppositories may be made for example by mixing with carriers provided for this purpose, such as neutral fats or polyethyleneglycol or the derivatives thereof.
  • the finely ground active substance, lactose and some of the corn starch are mixed together.
  • the mixture is screened, then moistened with a solution of polyvinylpyrrolidone in water, kneaded, wet-granulated and dried.
  • the granules, the remaining corn starch and the magnesium stearate are screened and mixed together.
  • the mixture is compressed to produce tablets of suitable shape and size.
  • the finely ground active substance, some of the corn starch, lactose, microcrystalline cellulose and polyvinylpyrrolidone are mixed together, the mixture is screened and worked with the remaining corn starch and water to form a granulate which is dried and screened.
  • the sodium-carboxymethyl starch and the magnesium stearate are added and mixed in and the mixture is compressed to form tablets of a suitable size.
  • the active substance, corn starch, lactose and polyvinylpyrrolidone are thoroughly mixed and moistened with water.
  • the moist mass is pushed through a screen with a 1 mm mesh size, dried at about 45°C and the granules are then passed through the same screen.
  • convex tablet cores with a diameter of 6 mm are compressed in a tablet-making machine .
  • the tablet cores thus produced are coated in known manner with a covering consisting essentially of sugar and talc.
  • the finished coated tablets are polished with wax.
  • the substance and corn starch are mixed and moistened with water.
  • the moist mass is screened and dried.
  • the dry granules are screened and mixed with magnesium stearate.
  • the finished mixture is packed into size 1 hard gelatine capsules.
  • the hard fat is melted.
  • the ground active substance is homogeneously dispersed. It is cooled to 38°C and poured into slightly chilled suppository moulds.
  • the compounds of formula (I) are administered in form of specific film coated tablets. Examples of these preferred formulations are listed below.
  • the film coated tablets listed below can be manufactured according to procedures known in the art (see hereto WO 03/097058).

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PCT/EP2006/067757 2005-10-29 2006-10-25 Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders Ceased WO2007048803A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA2626134A CA2626134C (en) 2005-10-29 2006-10-25 Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders
JP2008537094A JP2009513604A (ja) 2005-10-29 2006-10-25 月経前障害及び他の女性の性的障害治療用のベンゾイミダゾロン誘導体
US12/091,848 US7923449B2 (en) 2005-10-29 2006-10-25 Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders
EP06807537A EP1945214A1 (en) 2005-10-29 2006-10-25 Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05023717.1 2005-10-29
EP05023717 2005-10-29

Publications (1)

Publication Number Publication Date
WO2007048803A1 true WO2007048803A1 (en) 2007-05-03

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PCT/EP2006/067757 Ceased WO2007048803A1 (en) 2005-10-29 2006-10-25 Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders

Country Status (5)

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US (1) US7923449B2 (https=)
EP (1) EP1945214A1 (https=)
JP (1) JP2009513604A (https=)
CA (1) CA2626134C (https=)
WO (1) WO2007048803A1 (https=)

Cited By (10)

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US7420057B2 (en) 2001-08-02 2008-09-02 Boehringer Ingelheim Pharma Kg Stable polymorph of flibanserin
US7923449B2 (en) 2005-10-29 2011-04-12 Boehringer Ingelheim International Gmbh Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders
US8227476B2 (en) 2005-08-03 2012-07-24 Sprout Pharmaceuticals, Inc. Use of flibanserin in the treatment of obesity
US8512748B2 (en) 2006-08-25 2013-08-20 Boehringer Ingelheim International Gmbh Controlled release system and method for manufacturing the same
US8545886B2 (en) 2006-08-14 2013-10-01 Boehringer Ingelheim International Gmbh Extended release tablet formulations of flibanserin and method for manufacturing the same
US8658207B2 (en) 2006-08-14 2014-02-25 Boehringer Ingelheim International Gmbh Extended release tablet formulations of flibanserin and method for manufacturing the same
US9763936B2 (en) 2006-06-30 2017-09-19 Sprout Pharmaceuticals, Inc. Flibanserin for the treatment of urinary incontinence and related diseases
US9782403B2 (en) 2001-10-20 2017-10-10 Sprout Pharmaceuticals, Inc. Treating sexual desire disorders with flibanserin
US10166230B2 (en) 2007-09-12 2019-01-01 Sprout Pharmaceuticals Inc. Treatment of vasomotor symptoms
US10675280B2 (en) 2001-10-20 2020-06-09 Sprout Pharmaceuticals, Inc. Treating sexual desire disorders with flibanserin

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US20030060475A1 (en) * 2001-08-10 2003-03-27 Boehringer Ingelheim Pharma Kg Method of using flibanserin for neuroprotection
US20040048877A1 (en) * 2002-05-22 2004-03-11 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical compositions containing flibanserin
US20050239798A1 (en) * 2004-04-22 2005-10-27 Boehringer Ingelheim Pharmaceuticals, Inc. Method for the treatment of premenstrual and other female sexual disorders
US20070105869A1 (en) * 2005-11-08 2007-05-10 Stephane Pollentier Use of flibanserin for the treatment of pre-menopausal sexual desire disorders
BRPI0712039A2 (pt) * 2006-05-09 2011-12-20 Boehringer Ingelheim Int uso de flibanserina para o tratamento de distúrbios de desejo sexual pós-menopausa
US20090318469A1 (en) * 2006-07-14 2009-12-24 Boehringer Ingelheim International Gmbh Use of Flibanserin for the Treatment of Sexual Disorders in Females
JP2010513390A (ja) * 2006-12-20 2010-04-30 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 混合セロトニン受容体親和性を有する硫酸化ベンズイミダゾロン誘導体
WO2008090742A1 (ja) * 2007-01-23 2008-07-31 National University Corporation Hokkaido University 眼疾患モデル用非ヒト動物

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