DK2155200T3 - Krystallinsk form af et carbamoyl-cyclohexan-derivat - Google Patents
Krystallinsk form af et carbamoyl-cyclohexan-derivat Download PDFInfo
- Publication number
- DK2155200T3 DK2155200T3 DK08755214.7T DK08755214T DK2155200T3 DK 2155200 T3 DK2155200 T3 DK 2155200T3 DK 08755214 T DK08755214 T DK 08755214T DK 2155200 T3 DK2155200 T3 DK 2155200T3
- Authority
- DK
- Denmark
- Prior art keywords
- crystalline form
- piperazin
- dichlorophenyl
- ethyl
- dimethyl
- Prior art date
Links
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical class NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 title claims description 4
- GPPJWWMREQHLQT-BHQIMSFRSA-N cariprazine hydrochloride Chemical compound Cl.C1C[C@@H](NC(=O)N(C)C)CC[C@@H]1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 GPPJWWMREQHLQT-BHQIMSFRSA-N 0.000 claims description 40
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- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 1
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Classifications
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- A61K31/4965—Non-condensed pyrazines
-
- A—HUMAN NECESSITIES
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- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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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
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (12)
- KRYSTALLINSK FORM AF ET CARBAMOYL-CYCLOHEXAN-DERIVAT Patentkrav1. Krystallinsk form af trans-1{4-[2-[4-(2,3-dichlorphenyl)-piperazin-l-yl]-ethyl]-cyclohexyl}-3,3-dimethyl-urinstof- hydrochlorici (form III) med et røntgenpulverdiffraktionsmønster (CuKa-stråling), der omfatter karakteristiske toppe ved 4,1, 12,3, 16,5 og 17,4 ± 0,2 grader 29,
- 2. Krystallinsk form ifølge krav 1, som har et røntgenpulverdiffraktionsmønster (CuKa-stråling) som vist i figur ri
- 3. Krystallinsk form ifølge krav 1, som har en smelteendoterm ved 2 60 °C som bestemt ved DSC (opvarmnings hastighed på 10 °C/min) .
- 4. Fremgangsmåde ti l fremstilling af den krysta llinske form ifølge krav 1, hvilken fremgangsmåde omfatter: (i) tilsætning af trans-1{4-[2-[4-(2,3-dichlorphenyl)-piperazin-1-y1]-ethy1]-c yc1ohexy1}-3,3-dimet hy1-urinstof-hydrochlorid til pyridin; og (ii) præcipitation af den krystallinske form ud fra opløsningen,
- 5. Fremgangsmåde ifølge krav 4, hvor blandingen i trin (i) opvarmes til en temperatur på 30 °C til 50 °C.
- 6. Fremgangsmåde ifølge krav 4, hvor trin (i) omfatter danne Ise af en mættet opløsning,
- 7. Fremgangsmåde ifølge krav 4, der yderligere omfatter (iii) isolering af den krystallinske form,
- 8. Fremgangsmåde ifølge krav 7, hvor trin (iii) omfatter (a) filtrering af det i trin (ii) dannede præcipitat og (b) tørring af den krystallinske form,
- 9. Farmaceutisk præparat, der omfatter den krystallinske form ifølge et hvilket som helst af kravene 1-3,
- 10. Krystallinsk form ifølge et hvilket som helst af kravene 1-3 til anvendelse ved behandling og/eller forebyggelse af en tilstand, der er valgt blandt skizofreni, skizoaffektive lidelser, kognitiv svækkelse, som ledsager skizofreni, milde til moderate kognitive svigt, demens, psykotiske tilstande, som er associeret med demens, psykotisk depression, mani, akut mani, bipolar lidelse, paranoide og deliriske lidelser, dyskinetiske lidelser såsom Parkinsons sygdom, neuroleptisk induceret parkinsonisme, depression, angst og stofmisbrug.
- 11. Krystallinsk form til anvendelse ifølge krav 10, hvor tilstanden er skizofreni.
- 12. Krystallinsk form til anvendelse ifølge krav 10, hvor tilstanden er akut mani.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91738307P | 2007-05-11 | 2007-05-11 | |
| PCT/US2008/063181 WO2008141135A1 (en) | 2007-05-11 | 2008-05-09 | Novel solvate and crystalline forms of carbamoyl-cyclohexane derivatives |
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| Publication Number | Publication Date |
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| DK2155200T3 true DK2155200T3 (da) | 2017-03-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK08755214.7T DK2155200T3 (da) | 2007-05-11 | 2008-05-09 | Krystallinsk form af et carbamoyl-cyclohexan-derivat |
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| Country | Link |
|---|---|
| US (2) | US7829569B2 (da) |
| EP (1) | EP2155200B1 (da) |
| JP (2) | JP2010526832A (da) |
| KR (2) | KR20150023937A (da) |
| CN (1) | CN101801381B (da) |
| AU (1) | AU2008251520B2 (da) |
| CA (2) | CA2756796C (da) |
| CY (1) | CY1118553T1 (da) |
| DK (1) | DK2155200T3 (da) |
| EA (1) | EA017732B1 (da) |
| ES (1) | ES2617671T3 (da) |
| HR (1) | HRP20170222T1 (da) |
| HU (1) | HUE033357T2 (da) |
| LT (1) | LT2155200T (da) |
| MY (1) | MY148643A (da) |
| PL (1) | PL2155200T3 (da) |
| PT (1) | PT2155200T (da) |
| SI (1) | SI2155200T1 (da) |
| WO (1) | WO2008141135A1 (da) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| HUP0700370A2 (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 of acute mania |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| US20110059980A1 (en) * | 2008-02-21 | 2011-03-10 | Yasuaki Oobayashi | Solid preparation for oral administration |
| 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 |
| HUP0800765A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Nyrt | A new process for the preparation of piperazine derivatives and their hydrochloric salts |
| HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
| US8489333B2 (en) | 2009-05-07 | 2013-07-16 | Halliburton Energy Services, Inc. | Device orientation determination |
| WO2012063246A1 (en) * | 2010-11-11 | 2012-05-18 | Mapi Pharma Ltd. | Amorphous form of lurasidone hydrochloride |
| US8981095B2 (en) | 2011-07-28 | 2015-03-17 | Mapi Pharma Ltd. | Intermediate compounds and process for the preparation of lurasidone and salts thereof |
| US8912197B2 (en) | 2012-08-20 | 2014-12-16 | Forest Laboratories Holdings Ltd. | Crystalline form of carbamoyl-cyclohexane derivatives |
| 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 |
| US20170128981A1 (en) * | 2015-11-09 | 2017-05-11 | Delavan Inc | Bulk metallic glass components |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation 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 |
| CN111712486B (zh) * | 2018-09-21 | 2024-09-13 | 上海诚妙医药科技有限公司 | 卡利拉嗪盐酸盐的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 |
| TWI908864B (zh) * | 2020-08-26 | 2025-12-21 | 大陸商上海雲晟研新生物科技有限公司 | 卡利拉嗪藥物組合物、製備方法及應用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6566550B2 (en) | 2001-06-21 | 2003-05-20 | Pfizer Inc | Substituted aromatic ethers as inhibitors of glycine transport |
| HU227534B1 (en) * | 2003-08-04 | 2011-08-29 | Richter Gedeon Nyrt | (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them |
| DE102004047517A1 (de) * | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
| GT200600414A (es) * | 2005-09-12 | 2007-09-20 | Sal de glucuranato de compuesto de piperazine | |
| HU230748B1 (hu) * | 2007-05-11 | 2018-02-28 | Richter Gedeon Nyrt | Új piperazin só és előállítási eljárása |
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- 2008-05-09 KR KR20157002948A patent/KR20150023937A/ko not_active Ceased
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- 2008-05-09 EA EA200901514A patent/EA017732B1/ru unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2014129386A (ja) | 2014-07-10 |
| LT2155200T (lt) | 2017-02-10 |
| EP2155200A1 (en) | 2010-02-24 |
| EP2155200A4 (en) | 2012-01-04 |
| KR20100027137A (ko) | 2010-03-10 |
| ES2617671T3 (es) | 2017-06-19 |
| US20090030007A1 (en) | 2009-01-29 |
| CA2756796A1 (en) | 2008-11-20 |
| PL2155200T3 (pl) | 2017-06-30 |
| CY1118553T1 (el) | 2017-07-12 |
| EP2155200B1 (en) | 2016-12-07 |
| CN101801381B (zh) | 2013-08-14 |
| PT2155200T (pt) | 2017-02-21 |
| JP2010526832A (ja) | 2010-08-05 |
| WO2008141135A1 (en) | 2008-11-20 |
| US20110028722A1 (en) | 2011-02-03 |
| EA200901514A1 (ru) | 2010-04-30 |
| AU2008251520B2 (en) | 2014-03-06 |
| EA017732B1 (ru) | 2013-02-28 |
| CN101801381A (zh) | 2010-08-11 |
| US8609665B2 (en) | 2013-12-17 |
| CA2756796C (en) | 2018-05-22 |
| CA2687078C (en) | 2012-04-10 |
| CA2687078A1 (en) | 2008-11-20 |
| MY148643A (en) | 2013-05-15 |
| HK1145148A1 (en) | 2011-04-08 |
| KR20150023937A (ko) | 2015-03-05 |
| AU2008251520A1 (en) | 2008-11-20 |
| HRP20170222T1 (hr) | 2017-04-07 |
| HUE033357T2 (en) | 2017-11-28 |
| SI2155200T1 (sl) | 2017-04-26 |
| US7829569B2 (en) | 2010-11-09 |
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