PT2358690E - Sal piperazina e um processo para a preparação do mesmo - Google Patents
Sal piperazina e um processo para a preparação do mesmo Download PDFInfo
- Publication number
- PT2358690E PT2358690E PT09797145T PT09797145T PT2358690E PT 2358690 E PT2358690 E PT 2358690E PT 09797145 T PT09797145 T PT 09797145T PT 09797145 T PT09797145 T PT 09797145T PT 2358690 E PT2358690 E PT 2358690E
- Authority
- PT
- Portugal
- Prior art keywords
- trans
- tert
- butoxycarbonyl
- cyclohexyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000004885 piperazines Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 10
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- UDQMXYJSNNCRAS-UHFFFAOYSA-N 2,3-dichlorophenylpiperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1Cl UDQMXYJSNNCRAS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 7
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 12
- LDQCWGIXZGDJNL-IYARVYRRSA-N chembl3085821 Chemical compound C1C[C@@H](NC(=O)OC(C)(C)C)CC[C@@H]1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 LDQCWGIXZGDJNL-IYARVYRRSA-N 0.000 claims description 8
- 238000002955 isolation Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- -1 2,3-dichlorophenyl Chemical group 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CYQFNNSFAGXCEC-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)piperazine;hydrochloride Chemical compound [Cl-].ClC1=CC=CC(N2CC[NH2+]CC2)=C1Cl CYQFNNSFAGXCEC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101150049660 DRD2 gene Proteins 0.000 description 1
- XJISEKYRACFXDF-BTTFERLTSA-N O.Cl.Cl.C1C[C@@H](N)CC[C@@H]1CCN1C(C=2C(=C(Cl)C=CC=2)Cl)CNCC1 Chemical compound O.Cl.Cl.C1C[C@@H](N)CC[C@@H]1CCN1C(C=2C(=C(Cl)C=CC=2)Cl)CNCC1 XJISEKYRACFXDF-BTTFERLTSA-N 0.000 description 1
- MYFGOYKKTHBBQT-SRWQXTDJSA-N O.Cl.Cl.N[C@H]1CC[C@H](CCN2CCN(CC2)c2cccc(Cl)c2Cl)CC1 Chemical compound O.Cl.Cl.N[C@H]1CC[C@H](CCN2CCN(CC2)c2cccc(Cl)c2Cl)CC1 MYFGOYKKTHBBQT-SRWQXTDJSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0800763A HU230067B1 (hu) | 2008-12-17 | 2008-12-17 | Új piperazin só és eljárás előállítására |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT2358690E true PT2358690E (pt) | 2016-06-03 |
Family
ID=89988672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT09797145T PT2358690E (pt) | 2008-12-17 | 2009-12-17 | Sal piperazina e um processo para a preparação do mesmo |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US8569496B2 (https=) |
| EP (1) | EP2358690B1 (https=) |
| JP (1) | JP5735923B2 (https=) |
| CN (1) | CN102256953B (https=) |
| AU (1) | AU2009329294B2 (https=) |
| BR (1) | BRPI0923007B8 (https=) |
| CA (1) | CA2743924C (https=) |
| DK (1) | DK2358690T3 (https=) |
| EA (1) | EA019024B1 (https=) |
| ES (1) | ES2573957T3 (https=) |
| GE (1) | GEP20125711B (https=) |
| HR (1) | HRP20160726T1 (https=) |
| HU (2) | HU230067B1 (https=) |
| IL (1) | IL212639A0 (https=) |
| MX (1) | MX2011006591A (https=) |
| NZ (1) | NZ592907A (https=) |
| PL (1) | PL2358690T3 (https=) |
| PT (1) | PT2358690E (https=) |
| SI (1) | SI2358690T1 (https=) |
| TW (1) | TWI448455B (https=) |
| UA (1) | UA104163C2 (https=) |
| WO (1) | WO2010070369A1 (https=) |
Families Citing this family (17)
| 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 |
| US7875610B2 (en) * | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| CA2715760C (en) * | 2008-02-21 | 2017-06-13 | Mitsubishi Tanabe Pharma Corporation | Solid preparation for oral administration of cariprazine hydrochloride |
| RS53866B1 (sr) | 2008-07-16 | 2015-08-31 | Richter Gedeon Nyrt. | Farmaceutske formulacije koje sadrže ligande dopaminskih receptora |
| 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 |
| ITMI20131693A1 (it) | 2013-10-14 | 2015-04-15 | Chemo Res S L | Derivati della 1,4-cicloesilammina e loro preparazione |
| CN104496854B (zh) * | 2015-01-06 | 2017-09-22 | 上海医药工业研究院 | 3‑环己基‑1,1‑二甲基脲类化合物及其制备方法和应用 |
| HU231173B1 (hu) | 2016-07-08 | 2021-06-28 | Richter Gedeon Nyrt. | Ipari eljárás cariprazine előállítására |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
| CN111269199B (zh) * | 2018-12-05 | 2022-04-08 | 浙江京新药业股份有限公司 | 一种卡利拉嗪的制备方法 |
| US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
| CN111892556A (zh) * | 2019-05-06 | 2020-11-06 | 北京万全德众医药生物技术有限公司 | 新的卡利拉嗪制备方法 |
| CN110372557B (zh) * | 2019-08-06 | 2021-05-18 | 上海勋和医药科技有限公司 | 环己烷胺类d3/d2受体部分激动剂 |
| CN114539185B (zh) * | 2020-11-24 | 2024-12-24 | 上海新礼泰药业有限公司 | 一种卡利拉嗪及其中间体的制备方法 |
| HUP2100108A1 (hu) | 2021-03-12 | 2022-09-28 | Richter Gedeon Nyrt | Eljárás és berendezés gyógyászatilag alkalmazható piperazin származékok folyamatos áramú, áramlásos konszekutív redukálással történõ elõállítására |
| CN119874636A (zh) * | 2025-01-16 | 2025-04-25 | 鲁南制药集团股份有限公司 | 一种卡利拉嗪的制备方法 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4957921A (en) | 1989-12-06 | 1990-09-18 | Warner-Lambert Company | Substituted cyclohexanols as central nervous system agents |
| US5047406A (en) | 1989-12-06 | 1991-09-10 | Warner-Lambert Co. | Substituted cyclohexanols as central nervous system agents |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| ES2293638T3 (es) | 1994-03-25 | 2008-03-16 | Isotechnika, Inc. | Mejora de la eficacia de farmacos por deuteracion. |
| WO1997011070A1 (en) | 1995-09-22 | 1997-03-27 | Warner-Lambert Company | Substituted cyclohexylamines as central nervous system agents |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| BR9909277A (pt) | 1998-03-31 | 2001-10-16 | Acadia Pharm Inc | Compostos com atividade em receptores muscarìnicos |
| SE9802208D0 (sv) | 1998-06-22 | 1998-06-22 | Astra Pharma Inc | Novel compounds |
| JP2000191570A (ja) * | 1998-12-24 | 2000-07-11 | Sumitomo Chem Co Ltd | ヒドロキシフェニルプロパノール類の製造法 |
| US6489341B1 (en) | 1999-06-02 | 2002-12-03 | Sepracor Inc. | Methods for the treatment of neuroleptic and related disorders using sertindole derivatives |
| PL364640A1 (en) | 2001-02-27 | 2004-12-13 | Ortho-Mcneil Pharmaceutical, Inc. | Carbamate compounds for use in preventing or treating bipolar disorder |
| US6566550B2 (en) | 2001-06-21 | 2003-05-20 | Pfizer Inc | Substituted aromatic ethers as inhibitors of glycine transport |
| 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 |
| SE0200301D0 (sv) | 2002-02-01 | 2002-02-01 | Axon Biochemicals Bv | Thio-carbostyril derivative |
| US6833459B2 (en) * | 2002-04-26 | 2004-12-21 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of thiazole intermediate |
| US6919342B2 (en) | 2003-06-05 | 2005-07-19 | Abbott Gmbh & Co. Kg | Triazole compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
| 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 |
| HUP0500170A3 (en) | 2005-02-03 | 2007-11-28 | Richter Gedeon Nyrt | Piperazine derivatives, process for producing them and pharmaceutical compositions containing them |
| GT200600414A (es) | 2005-09-12 | 2007-09-20 | Sal de glucuranato de compuesto de piperazine | |
| JP2008001633A (ja) * | 2006-06-22 | 2008-01-10 | Showa Denko Kk | テトラヒドロピランを溶媒とする塩化アルミニウム存在下での水素化ホウ素化合物による還元反応 |
| HUP0600809A3 (en) * | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New phenylsulfamoyl-benzamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| HU230748B1 (hu) | 2007-05-11 | 2018-02-28 | Richter Gedeon Nyrt | Új piperazin só és előállítási eljárása |
| EP2155200B1 (en) | 2007-05-11 | 2016-12-07 | Richter Gedeon Nyrt. | Crystalline form of a carbamoyl-cyclohexane derivative |
| 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 |
| AR070513A1 (es) | 2007-08-01 | 2010-04-14 | Lundbeck & Co As H | Uso de abridores de canales de potasio kcnq para reducir los sintomas o tratar desordenes o afecciones en las cuales se encuentra anulado el sis-tema dopaminergico como por ejemplo esquizofrenia y trastorno depresivo mayor |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| CA2715760C (en) | 2008-02-21 | 2017-06-13 | Mitsubishi Tanabe Pharma Corporation | Solid preparation for oral administration of cariprazine hydrochloride |
| RS53866B1 (sr) | 2008-07-16 | 2015-08-31 | Richter Gedeon Nyrt. | Farmaceutske formulacije koje sadrže ligande dopaminskih receptora |
| 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 |
-
2008
- 2008-12-17 HU HU0800763A patent/HU230067B1/hu not_active IP Right Cessation
-
2009
- 2009-12-15 TW TW098142934A patent/TWI448455B/zh active
- 2009-12-17 AU AU2009329294A patent/AU2009329294B2/en active Active
- 2009-12-17 HR HRP20160726TT patent/HRP20160726T1/hr unknown
- 2009-12-17 UA UAA201109013A patent/UA104163C2/ru unknown
- 2009-12-17 HU HUE09797145A patent/HUE029667T2/en unknown
- 2009-12-17 JP JP2011541613A patent/JP5735923B2/ja active Active
- 2009-12-17 NZ NZ592907A patent/NZ592907A/xx unknown
- 2009-12-17 WO PCT/HU2009/000108 patent/WO2010070369A1/en not_active Ceased
- 2009-12-17 GE GEAP200912300A patent/GEP20125711B/en unknown
- 2009-12-17 PT PT09797145T patent/PT2358690E/pt unknown
- 2009-12-17 SI SI200931453A patent/SI2358690T1/sl unknown
- 2009-12-17 EP EP09797145.1A patent/EP2358690B1/en active Active
- 2009-12-17 US US13/140,232 patent/US8569496B2/en active Active
- 2009-12-17 DK DK09797145.1T patent/DK2358690T3/en active
- 2009-12-17 CA CA2743924A patent/CA2743924C/en not_active Expired - Fee Related
- 2009-12-17 MX MX2011006591A patent/MX2011006591A/es active IP Right Grant
- 2009-12-17 ES ES09797145.1T patent/ES2573957T3/es active Active
- 2009-12-17 BR BRPI0923007A patent/BRPI0923007B8/pt active IP Right Grant
- 2009-12-17 CN CN200980150465.2A patent/CN102256953B/zh active Active
- 2009-12-17 EA EA201170810A patent/EA019024B1/ru unknown
- 2009-12-17 PL PL09797145.1T patent/PL2358690T3/pl unknown
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2011
- 2011-05-03 IL IL212639A patent/IL212639A0/en active IP Right Grant
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