CA2597016C - Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine - Google Patents

Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine Download PDF

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Publication number
CA2597016C
CA2597016C CA2597016A CA2597016A CA2597016C CA 2597016 C CA2597016 C CA 2597016C CA 2597016 A CA2597016 A CA 2597016A CA 2597016 A CA2597016 A CA 2597016A CA 2597016 C CA2597016 C CA 2597016C
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CA
Canada
Prior art keywords
chlorophenyl
propoxy
propyl
piperidine
group
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
Application number
CA2597016A
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English (en)
French (fr)
Other versions
CA2597016A1 (en
Inventor
Manuel M. Raga
Juan Sallares
Marta Guerrero
Antonio Guglietta
Jean-Charles Schwartz
Jean-Michel Arrang
Jeanne-Marie Lecomte
Xavier Ligneau
Walter Schunack
Holger Stark
Charon Robin Ganellin
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Bioprojet SC
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Bioprojet SC
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Application filed by Bioprojet SC filed Critical Bioprojet SC
Publication of CA2597016A1 publication Critical patent/CA2597016A1/en
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Publication of CA2597016C publication Critical patent/CA2597016C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • A61P15/08—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
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P19/00—Drugs for skeletal disorders
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Reproductive Health (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Otolaryngology (AREA)
  • Diabetes (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Obesity (AREA)
  • Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Anesthesiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Hematology (AREA)
  • Gynecology & Obstetrics (AREA)
CA2597016A 2005-02-10 2006-02-06 Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine Expired - Lifetime CA2597016C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05100942A EP1690858B1 (en) 2005-02-10 2005-02-10 Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine
EP05100942.1 2005-02-10
PCT/EP2006/050703 WO2006084833A1 (en) 2005-02-10 2006-02-06 Monohydrochloride salt of 1- [3- [3- (4-chlorophenyl) propoxy] propyl] -piperidine

Publications (2)

Publication Number Publication Date
CA2597016A1 CA2597016A1 (en) 2006-08-17
CA2597016C true CA2597016C (en) 2013-01-15

Family

ID=34938687

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2597016A Expired - Lifetime CA2597016C (en) 2005-02-10 2006-02-06 Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine

Country Status (22)

Country Link
US (2) US8207197B2 (enExample)
EP (2) EP1690858B1 (enExample)
JP (1) JP5072604B2 (enExample)
KR (1) KR101344271B1 (enExample)
CN (1) CN101155793B (enExample)
AR (1) AR054734A1 (enExample)
AT (2) ATE391716T1 (enExample)
CA (1) CA2597016C (enExample)
CY (1) CY1108428T1 (enExample)
DE (2) DE602005005941D1 (enExample)
DK (1) DK1846384T3 (enExample)
ES (1) ES2309948T3 (enExample)
HR (1) HRP20080446T3 (enExample)
ME (1) ME01103B (enExample)
MX (1) MX2007009574A (enExample)
PL (1) PL1846384T3 (enExample)
PT (1) PT1846384E (enExample)
RS (1) RS50624B (enExample)
SI (1) SI1846384T1 (enExample)
TW (1) TWI393711B (enExample)
UY (1) UY29369A1 (enExample)
WO (1) WO2006084833A1 (enExample)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
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EP2167096A4 (en) * 2007-06-13 2010-07-14 Cypress Bioscience Inc IMPROVING TOLERANCE TO MIRTAZAPINE AND A SECOND ACTIVE INGREDIENT BY THE COMBINED USE OF THEM
RU2011137419A (ru) 2009-02-11 2013-03-20 Суновион Фармасьютикалз Инк. Обратные агонисты и антагонисты гистамина н3 и способы их применения
KR20120035183A (ko) 2009-06-10 2012-04-13 선오비온 파마슈티컬스 인코포레이티드 히스타민 ｈ3 역 작용제 및 길항제, 및 이의 사용 방법
CA2772522A1 (en) 2009-09-11 2011-03-17 Sunovion Pharmaceuticals Inc. Histamine h3 inverse agonists and antagonists and methods of use thereof
WO2014199935A1 (ja) * 2013-06-10 2014-12-18 株式会社エム・エス・エス 小胞体ストレスシグナルを抑制することによる，薬剤の副作用としての体重増加や肥満を防止するために用いられる肥満防止剤
CN103435575A (zh) * 2013-08-06 2013-12-11 中国人民解放军军事医学科学院毒物药物研究所 1-（ 3-（ 3-（ 4-氯苯基）丙氧基）丙基）哌啶盐酸盐的制备方法
CN104447620B (zh) * 2014-11-28 2016-05-04 瑞阳制药有限公司 1-[3-[3-(4-氯苯基)丙氧基]丙基]-哌啶盐酸盐的制备方法
EP3239138A1 (en) 2016-04-25 2017-11-01 Sandoz Ag Hydrogen fumarate salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]piperidine
WO2020092604A1 (en) * 2018-10-30 2020-05-07 Concert Pharmaceuticals, Inc. Deuterated pitolisant
IT201900013941A1 (it) 2019-08-05 2021-02-05 Procos Spa PROCESSO PER LA SINTESI DI PITOLISANT HCl
CN110804026B (zh) * 2019-11-18 2022-04-01 苏州永健生物医药有限公司 1- (3- (3-（4-氯苯基）丙氧基)丙基)哌啶盐酸盐的合成方法
US11623920B2 (en) 2021-06-07 2023-04-11 Nuray Chemicals Private Limited Process for preparing pitolisant hydrochloride and solid-state forms thereof
US11945788B2 (en) 2021-06-07 2024-04-02 Nuray Chemicals Private Limited Process for preparing pitolisant hydrochloride and solid-state forms thereof
EP4457219A4 (en) * 2021-12-29 2025-12-10 Biophore India Pharmaceuticals Pvt Ltd SOLID FORMS OF 1-3-[3-(4-CHLOROPHENYL)PROPOXY]PROPYL PIPERIDINE HYDROCHLORIDE AND THEIR PREPARATION PROCESS
US20250281475A1 (en) * 2022-05-04 2025-09-11 Msn Laboratories Private Limited, R & D Center A pharmaceutical composition of pitolisant hydrochloride and their process for the preparation
WO2024084379A1 (en) * 2022-10-17 2024-04-25 Biophore India Pharmaceuticals Pvt. Ltd A NOVEL PROCESS FOR THE PREPARATION OF AMORPHOUS SOLID DISPERSION OF 1-{3-[3-(4-CHLOROPHENYL) PROPOXY] PROPYL} PIPERIDINE, HYDROCHLORIDE WITH HYDROXYPROPYL BETA-CYCLODEXTRIN (HPβCD)
EP4374854A1 (en) * 2022-11-28 2024-05-29 Alfred E. Tiefenbacher (GmbH & Co. KG) Pharmaceutical mixture comprising amorphous pitolisant
CN121175294A (zh) 2023-03-31 2025-12-19 生物计划制药公司 盐酸替洛利生的多晶型形式
TW202535386A (zh) 2023-10-16 2025-09-16 法商拜爾普羅傑特醫藥有限公司 腸溶包衣必托里賽（ｐｉｔｏｌｉｓａｎｔ）調配物及使用方法
EP4681704A1 (en) 2024-07-18 2026-01-21 BIOPROJET Pharma New formulations of pitolisant
EP4732903A1 (en) 2024-10-28 2026-04-29 BIOPROJET Pharma Co-crystals of pitolisant hydrochloride

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
EP0982300A3 (en) * 1998-07-29 2000-03-08 Societe Civile Bioprojet Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications

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JP5072604B2 (ja) 2012-11-14
ME01103B (me) 2013-03-20
US8207197B2 (en) 2012-06-26
CA2597016A1 (en) 2006-08-17
DK1846384T3 (da) 2008-11-17
ATE391716T1 (de) 2008-04-15
EP1846384A1 (en) 2007-10-24
DE602006001938D1 (de) 2008-09-04
DE602005005941D1 (de) 2008-05-21
CY1108428T1 (el) 2014-04-09
PT1846384E (pt) 2008-10-21
US20120289546A1 (en) 2012-11-15
MX2007009574A (es) 2007-09-25
SI1846384T1 (sl) 2008-12-31
EP1846384B1 (en) 2008-07-23
EP1690858A1 (en) 2006-08-16
ATE402154T1 (de) 2008-08-15
TWI393711B (zh) 2013-04-21
WO2006084833A1 (en) 2006-08-17
KR20070101381A (ko) 2007-10-16
US8354430B2 (en) 2013-01-15
CN101155793A (zh) 2008-04-02
PL1846384T3 (pl) 2009-01-30
KR101344271B1 (ko) 2013-12-26
CN101155793B (zh) 2015-05-20
ES2309948T3 (es) 2008-12-16
HRP20080446T3 (en) 2008-10-31
UY29369A1 (es) 2006-05-31
EP1690858B1 (en) 2008-04-09
TW200639157A (en) 2006-11-16
JP2008530050A (ja) 2008-08-07
AR054734A1 (es) 2007-07-11
RS50624B (sr) 2010-06-30
US20080221162A1 (en) 2008-09-11

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