JP2008530050A5 - - Google Patents
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- Publication number
- JP2008530050A5 JP2008530050A5 JP2007554541A JP2007554541A JP2008530050A5 JP 2008530050 A5 JP2008530050 A5 JP 2008530050A5 JP 2007554541 A JP2007554541 A JP 2007554541A JP 2007554541 A JP2007554541 A JP 2007554541A JP 2008530050 A5 JP2008530050 A5 JP 2008530050A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- group
- butanol
- composition according
- chlorophenyl
- 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.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 230000001430 anti-depressive effect Effects 0.000 claims 5
- 239000000935 antidepressant agent Substances 0.000 claims 5
- 229940005513 antidepressants Drugs 0.000 claims 5
- 208000015114 central nervous system disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- 230000000561 anti-psychotic effect Effects 0.000 claims 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- XLFKECRRMPOAQS-UHFFFAOYSA-N 1-[3-[3-(4-chlorophenyl)propoxy]propyl]piperidine;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1CCCOCCCN1CCCCC1 XLFKECRRMPOAQS-UHFFFAOYSA-N 0.000 claims 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims 2
- 206010041349 Somnolence Diseases 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 229960000836 amitriptyline Drugs 0.000 claims 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims 2
- 229960004372 aripiprazole Drugs 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 229960004170 clozapine Drugs 0.000 claims 2
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 229960001785 mirtazapine Drugs 0.000 claims 2
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 2
- 229960005017 olanzapine Drugs 0.000 claims 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 229960002296 paroxetine Drugs 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 230000001107 psychogenic effect Effects 0.000 claims 2
- 229960004431 quetiapine Drugs 0.000 claims 2
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 229960001534 risperidone Drugs 0.000 claims 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 2
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 1
- 208000032140 Sleepiness Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 206010044302 Tracheitis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 208000021017 Weight Gain Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 208000008784 apnea Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000000718 duodenal ulcer Diseases 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 201000005917 gastric ulcer Diseases 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 208000014617 hemorrhoid Diseases 0.000 claims 1
- 230000002267 hypothalamic effect Effects 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 230000007803 itching Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 210000000754 myometrium Anatomy 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- NNACHAUCXXVJSP-UHFFFAOYSA-N pitolisant Chemical compound C1=CC(Cl)=CC=C1CCCOCCCN1CCCCC1 NNACHAUCXXVJSP-UHFFFAOYSA-N 0.000 claims 1
- 230000001817 pituitary effect Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 210000003296 saliva Anatomy 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 230000037321 sleepiness Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 210000002229 urogenital system Anatomy 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05100942.1 | 2005-02-10 | ||
| EP05100942A EP1690858B1 (en) | 2005-02-10 | 2005-02-10 | Monohydrochloride salt of 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-piperidine |
| PCT/EP2006/050703 WO2006084833A1 (en) | 2005-02-10 | 2006-02-06 | Monohydrochloride salt of 1- [3- [3- (4-chlorophenyl) propoxy] propyl] -piperidine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008530050A JP2008530050A (ja) | 2008-08-07 |
| JP2008530050A5 true JP2008530050A5 (enExample) | 2009-04-02 |
| JP5072604B2 JP5072604B2 (ja) | 2012-11-14 |
Family
ID=34938687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007554541A Active JP5072604B2 (ja) | 2005-02-10 | 2006-02-06 | １−［３−［３−（４−クロロフェニル）プロポキシ］プロピル］−ピペリジン一塩酸塩 |
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 (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SG173639A1 (en) | 2009-02-11 | 2011-09-29 | Sunovion Pharmaceuticals Inc | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| RU2011153723A (ru) | 2009-06-10 | 2013-07-20 | Суновион Фармасьютикалз Инк. | Обратные агонисты и антагонисты н3 рецепторов гистамина и способы их применения |
| US20110065694A1 (en) | 2009-09-11 | 2011-03-17 | Milan Chytil | 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 |
| US11945788B2 (en) | 2021-06-07 | 2024-04-02 | Nuray Chemicals Private Limited | Process for preparing pitolisant hydrochloride and solid-state forms thereof |
| US11623920B2 (en) | 2021-06-07 | 2023-04-11 | 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 |
| KR20250165426A (ko) | 2023-03-31 | 2025-11-25 | 바이오프로제 파르마 | 피톨리산트 염산염의 다형(多形) 형태 |
| WO2025082972A1 (en) | 2023-10-16 | 2025-04-24 | Bioprojet Pharma | Enteric coated pitolisant formulations and methods of use |
Family Cites Families (1)
| 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 |
-
2005
- 2005-02-10 DE DE602005005941T patent/DE602005005941D1/de not_active Expired - Lifetime
- 2005-02-10 EP EP05100942A patent/EP1690858B1/en not_active Expired - Lifetime
- 2005-02-10 AT AT05100942T patent/ATE391716T1/de not_active IP Right Cessation
-
2006
- 2006-02-06 DK DK06708050T patent/DK1846384T3/da active
- 2006-02-06 MX MX2007009574A patent/MX2007009574A/es active IP Right Grant
- 2006-02-06 RS RSP-2008/0482A patent/RS50624B/sr unknown
- 2006-02-06 PL PL06708050T patent/PL1846384T3/pl unknown
- 2006-02-06 EP EP06708050A patent/EP1846384B1/en active Active
- 2006-02-06 SI SI200630073T patent/SI1846384T1/sl unknown
- 2006-02-06 WO PCT/EP2006/050703 patent/WO2006084833A1/en not_active Ceased
- 2006-02-06 AT AT06708050T patent/ATE402154T1/de active
- 2006-02-06 ME MEP-2008-394A patent/ME01103B/me unknown
- 2006-02-06 CN CN200680008857.1A patent/CN101155793B/zh active Active
- 2006-02-06 ES ES06708050T patent/ES2309948T3/es active Active
- 2006-02-06 HR HR20080446T patent/HRP20080446T3/xx unknown
- 2006-02-06 DE DE602006001938T patent/DE602006001938D1/de active Active
- 2006-02-06 CA CA2597016A patent/CA2597016C/en active Active
- 2006-02-06 JP JP2007554541A patent/JP5072604B2/ja active Active
- 2006-02-06 PT PT06708050T patent/PT1846384E/pt unknown
- 2006-02-06 US US11/815,736 patent/US8207197B2/en active Active
- 2006-02-08 TW TW095104184A patent/TWI393711B/zh active
- 2006-02-08 AR ARP060100448A patent/AR054734A1/es not_active Application Discontinuation
- 2006-02-09 UY UY29369A patent/UY29369A1/es not_active Application Discontinuation
-
2007
- 2007-09-06 KR KR1020077020422A patent/KR101344271B1/ko active Active
-
2008
- 2008-10-21 CY CY20081101174T patent/CY1108428T1/el unknown
-
2012
- 2012-06-07 US US13/491,229 patent/US8354430B2/en active Active
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