HUE034796T2 - D2/D3 antagonista piperazin sók - Google Patents
D2/D3 antagonista piperazin sók Download PDFInfo
- Publication number
- HUE034796T2 HUE034796T2 HUE08750834A HUE08750834A HUE034796T2 HU E034796 T2 HUE034796 T2 HU E034796T2 HU E08750834 A HUE08750834 A HU E08750834A HU E08750834 A HUE08750834 A HU E08750834A HU E034796 T2 HUE034796 T2 HU E034796T2
- Authority
- HU
- Hungary
- Prior art keywords
- dichlorophenyl
- ethyl
- piperazine
- trans
- dimethylcarbamoyl
- Prior art date
Links
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- Physiology (AREA)
- Dermatology (AREA)
Claims (6)
- iwm ÁmMimmA pifiäzwä Pl ÏSS mú B!) I;< 2-(-1--(2J“iÉIôïffen)l}"pipcrazin~l”il]~etl!}~N>N"dhneülkarhamon“Cii!ÂeKi:!·' íámM: ^fiohidrokloÂéÂâgy hídnitjai és/vagy szölvé|at.:
- 3.. BljÂ.;p-l:;:%éîîÿpM::-Âinti vegyölet eleáliitáslfa azzal jél!emezy% hogy |442,3^IIÍÉÍ@nlÍÍ^!p8p|n-1 ~ií]~atd }~N,;M-4imötdkarbamoll--ci(ttö!3P^i{:~a:mia bázist megfeleld? Äfeöf m^tádósmek elegyében szuszpendáljuk, majd az elegyhéZ |Ι€Β| vagy annak a /m«-'4~(2~(4~(23-'dik!íSríeaílhpíparazm~l'-il]'etiI}-'N,N'-diá(etfika^ámölÍ> ciklobexi^aÄnk! gpdgibb bázissal. alkotott sóját, vagy azok oldatát adjuk, és adott çsotbmtr^MéÂp-'Ipiceôildéjàt beiöményitésse! nővé|jök és/vagy lehűljük, azután a kapott terméket szűréssel izoláljuk. 3, A 3, igénypont særlntl u|iras 3zzaljeikmezve5 hogy olyan HCl sutátkatmazunk, atndy a 0'ö/j.st''-4"|2"|4A223"diklórfenll}--pipera2Ín-!"il]-otíl}''M,N'-dimetilkarbamoil-cíklohexík ^imuâl^pifébBIM^i^Àëliâl 1 fiásra.
- 4.. Gyógyszerkészítmény, amely az 1. Igénypont szerinti vegyüíetet egy vagy több gyógyászatiig elfogadható segédanyaggal együtt tartalmazza.
- 5. Az 1. igénypont szerinti vegyidet dopamio receptor befolyásolását igénylő betegségek kezelésében vagy megelőzésében történő alkalmazása.0, Az 5, igénypont szerinti alkalmazás® szolgáló vegyi let, ahol a dópanbn teoeptor löpamin D* és/vagy dopamin Dr receptor.
- 7. Az 5. igénypont szerinti alkalmazásra szolgáló vegyölet, ahol a dopamirí receptor befolyásolását igénylő állapotok a szkizoiréma, a szkizo-affektív betegségek, a szkizoíféniát kísérő kognitív károsodás, az enyhétől a mérsékeltig terjedő kognitiv de&llek, & ddneneia, A dsfaénelâval tornái psziohotlkns állapotok, a p^iahtÄai depmsszió, a mánia, a p»Ä & têmmmÊiïml jàtô betegségek, valaonnt a im^âsitvarral jlte betegségek, mfimaonlyen à liaryaeoa-kbr, a neoi^lipten által kimitötípgrkía^Mííatüs, a depmsszib,: aaaDMeilses a deegliggösái> 8, M. !< igénypont szerinti vegyùlet fcrÂps h sided!}-N,Ndgneríikarbamí.si!'CÍkiohexil--arnÍ!'í monohktroklorkl só aohklrál (borm: I) (ormában,
- 9, A I:, Igénypont szerinti kristálvíbnna sassal jellemezve, bogy annak infravörös :§j^ktçumil^i::0l»feîi§l:SàViÉ:v^nàk;allI:l^ 293 ! ; 2914,2466; 1652; 1526; 956:284; 715 ! 0, A 8, igénypont szerinti kmtáiyíbnna azzal jeilen;ezve, hogy az 1. ábra szerinti az infravörös spektrommai rgnáelkegik, I L A 8. igénypont szerinti kristMyiirma aZMljeilémezve, bogy annak Bätnan spekttnmábari: jellemző rezgési 2933; 2914; 2864; 285«; 1578; 1458; 1052; 473 cm'5 ± 4 em'^sértiktápbnfányökban;, 12„ A 8, igénypont szerinti kr:(islá%feii8'(fc ami .Jellemezve begy a 2· ábra sgeriaíkll&snan: spektrummal .rendelkezik, ÍJ:> A |>, Igénypont szerinti Irlstályfartm mm jeiemazvá, boly Annák: Königen»· dillrdktogranpiban jellemzi relemák vannak a 6,6; 7,3:; 13,2; (4,2; 14,6; 16,9; 2 Ll ;:22,4¾ 24,8; 26,5; 26,6 ö * 0,2 *2ö szórási szögIriéfóe 14. A 8, Igénypont szerinti: kristályforma: azzal jellemezve, bogy a 3, #ra szerinti (bitttpin dí;icuktogrammal rendelkezik.
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HU0700339A HU230748B1 (hu) | 2007-05-11 | 2007-05-11 | Új piperazin só és előállítási eljárása |
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HU0700339A HU230748B1 (hu) | 2007-05-11 | 2007-05-11 | Új piperazin só és előállítási eljárása |
HUE08750834A HUE034796T2 (hu) | 2007-05-11 | 2008-05-13 | D2/D3 antagonista piperazin sók |
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HU0700339A HU230748B1 (hu) | 2007-05-11 | 2007-05-11 | Új piperazin só és előállítási eljárása |
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US (1) | US7943621B2 (hu) |
EP (1) | EP2155696B1 (hu) |
JP (1) | JP2010526861A (hu) |
KR (2) | KR20100018493A (hu) |
CN (1) | CN101679315B (hu) |
AP (1) | AP2009005012A0 (hu) |
AU (1) | AU2008249772B2 (hu) |
BR (1) | BRPI0811199A2 (hu) |
CA (1) | CA2684404C (hu) |
CO (1) | CO6241112A2 (hu) |
CY (1) | CY1119076T1 (hu) |
DK (1) | DK2155696T3 (hu) |
EA (1) | EA017270B1 (hu) |
EC (1) | ECSP099772A (hu) |
ES (1) | ES2628025T3 (hu) |
GE (1) | GEP20125522B (hu) |
HK (1) | HK1140473A1 (hu) |
HR (1) | HRP20170918T1 (hu) |
HU (2) | HU230748B1 (hu) |
IL (1) | IL201533A0 (hu) |
LT (1) | LT2155696T (hu) |
MA (1) | MA31434B1 (hu) |
MX (1) | MX2009012182A (hu) |
MY (1) | MY148078A (hu) |
NI (1) | NI200900203A (hu) |
NZ (1) | NZ580642A (hu) |
PL (1) | PL2155696T3 (hu) |
PT (1) | PT2155696T (hu) |
RS (1) | RS56036B1 (hu) |
SI (1) | SI2155696T1 (hu) |
TN (1) | TN2009000458A1 (hu) |
TW (1) | TWI424846B (hu) |
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Families Citing this family (23)
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---|---|---|---|---|
EA017732B1 (ru) * | 2007-05-11 | 2013-02-28 | Рихтер Гедеон Нирт. | Сольватная и кристаллическая формы гидрохлорида транс-1{4-[2-[4-(2,3-дихлорфенил)пиперазин-1-ил]этил]циклогексил}-3,3-диметилмочевины, способы их получения и их применение в фармацевтических композициях и способах лечения состояний, для которых необходима модуляция дофаминовых рецепторов |
HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
HUP0700369A2 (en) | 2007-05-24 | 2009-04-28 | Richter Gedeon Nyrt | Use of (thio)-carbamoyl-cyclohexane derivatives in the manufacture of a medicament for the treatment in the manufacture of a medicament for the treatment of schizophrenia |
EA018064B1 (ru) * | 2007-08-03 | 2013-05-30 | Рихтер Гедеон Нирт. | Способ лечения депрессии |
US7875610B2 (en) * | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
EA023972B1 (ru) * | 2008-02-21 | 2016-08-31 | Рихтер Гедеон Нирт. | Стабильный твёрдый препарат карипразина для перорального введения и способ его получения |
MY156288A (en) | 2008-07-16 | 2016-01-29 | Richter Gedeon Nyrt | Pharmaceutical formulations containing dopamine receptor ligands. |
HU230067B1 (hu) | 2008-12-17 | 2015-06-29 | Richter Gedeon Nyrt | Új piperazin só és eljárás előállítására |
HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
HUP0800765A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Nyrt | A new process for the preparation of piperazine derivatives and their hydrochloric salts |
US8912197B2 (en) | 2012-08-20 | 2014-12-16 | Forest Laboratories Holdings Ltd. | Crystalline form of carbamoyl-cyclohexane derivatives |
HU231227B1 (hu) | 2012-11-29 | 2022-03-28 | Richter Gedeon Nyrt. | Transz-4-{2-[4-(2,3-diklórfenil)-piperazin-1-il]-etil}N,N-dimetilkarbamoil-ciklohexilamin skizofrénia negatív tüneteinek kezelésére |
CN105218484B (zh) * | 2015-09-14 | 2018-02-23 | 安徽省逸欣铭医药科技有限公司 | 酒石酸卡利拉嗪及其制备方法和医药用途 |
CN106543105B (zh) * | 2015-09-22 | 2019-10-11 | 江苏恩华药业股份有限公司 | 一种盐酸卡利拉嗪晶型ⅳ及其制备方法 |
US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
WO2018229794A1 (en) | 2017-06-13 | 2018-12-20 | Cipla Limited | Amorphous form of cariprazine |
WO2019016828A1 (en) * | 2017-07-15 | 2019-01-24 | Msn Laboratories Private Limited, R&D Center | NOVEL PROCESSES FOR THE PREPARATION OF TRANS-N- {4- [2- [4- (2,3-DICHLOROPHENYL) PIPERAZIN-1-YL] ETHYL] CYCLOHEXYL} -N ', N'-DIMETHYLUMED HYDROCHLORIDE AND POLYMORPHS THIS ONE |
WO2020056929A1 (zh) * | 2018-09-21 | 2020-03-26 | 上海诚妙医药科技有限公司 | 卡利拉嗪盐酸盐的新晶型及其制备方法及其用途 |
HU231500B1 (hu) | 2019-04-10 | 2024-04-28 | Richter Gedeon Nyrt | Karbamoil-ciklohexán származékok autizmus spektrum betegség kezelésére |
US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
JP2023540056A (ja) | 2020-08-26 | 2023-09-21 | 上海雲晟研新生物科技有限公司 | カリプラジン薬用塩及びその結晶形、製造方法及び応用 |
WO2023077094A1 (en) * | 2021-10-28 | 2023-05-04 | Abbvie Inc. | Treatment of major depressive disorder |
WO2024072930A1 (en) * | 2022-09-30 | 2024-04-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dopamine d3/d2 receptor partial agonists for the treatment of neuropsychiatric disorders |
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HU227543B1 (en) * | 2001-09-28 | 2011-08-29 | Richter Gedeon Nyrt | N-[4-(2-piperazin- and 2-piperidin-1-yl-ethyl)-cyclohexyl]-sulfon- and sulfamides, process for their preparation, their use and pharmaceutical compositions containing them |
HU227534B1 (en) * | 2003-08-04 | 2011-08-29 | Richter Gedeon Nyrt | (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them |
HUP0500170A3 (en) * | 2005-02-03 | 2007-11-28 | Richter Gedeon Nyrt | Piperazine derivatives, process for producing them and pharmaceutical compositions containing them |
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