TW201002324A - Metabolites of (thio) carbamoyl-cyclohexane derivatives - Google Patents
Metabolites of (thio) carbamoyl-cyclohexane derivatives Download PDFInfo
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- TW201002324A TW201002324A TW097125708A TW97125708A TW201002324A TW 201002324 A TW201002324 A TW 201002324A TW 097125708 A TW097125708 A TW 097125708A TW 97125708 A TW97125708 A TW 97125708A TW 201002324 A TW201002324 A TW 201002324A
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- aryl
- alkyl
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- 239000002207 metabolite Substances 0.000 title claims abstract description 17
- JMMKXVYQBRGGJF-UHFFFAOYSA-N cyclohexanecarbothioamide Chemical class NC(=S)C1CCCCC1 JMMKXVYQBRGGJF-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 34
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- -1 cyano, cyclohexyl Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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Classifications
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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
- C07D295/12—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
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- 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
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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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- 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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- 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| PCT/HU2008/000046 WO2008142461A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Publications (1)
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|---|---|
| TW201002324A true TW201002324A (en) | 2010-01-16 |
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|---|---|---|---|
| TW097125708A TW201002324A (en) | 2007-05-18 | 2008-07-08 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
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| IL (1) | IL201534A0 (enExample) |
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| MX (1) | MX2009012371A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| WO2009104739A1 (ja) * | 2008-02-21 | 2009-08-27 | 田辺三菱製薬株式会社 | 経口投与用固形製剤 |
| UA104869C2 (uk) | 2008-07-16 | 2014-03-25 | Ріхтер Гедеон Нірт. | Фармацевтичні композиції, що містять ліганди рецептора дофаміну |
| 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 |
| ES2447295T3 (es) * | 2009-11-06 | 2014-03-11 | Sk Biopharmaceuticals Co., Ltd. | Métodos para el tratamiento del trastorno de déficit de atención/hiperactividad |
| WO2011060363A2 (en) * | 2009-11-16 | 2011-05-19 | Auspex Pharmaceuticals, Inc. | Cyclohexyl urea modulators of d2 receptors and/or d3 receptors |
| HUP0900790A2 (en) * | 2009-12-17 | 2011-09-28 | Richter Gedeon Nyrt | A new process for the preparation of piperazine and their hydrochloric salts |
| WO2014031162A1 (en) * | 2012-08-20 | 2014-02-27 | Forest Laboratories Holdings Limited | Crystalline form of carbamoyl-cyclohexane derivatives |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
| WO2018153297A1 (zh) * | 2017-02-24 | 2018-08-30 | 深圳市灵兰生物医药科技有限公司 | 新型多巴胺d3受体选择性配体及其制备方法和医药应用 |
| CN108586389B (zh) * | 2018-06-29 | 2020-06-12 | 成都福柯斯医药技术有限公司 | 一种合成卡利拉嗪的方法 |
| 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 |
| CN112239433B (zh) * | 2019-07-17 | 2024-05-14 | 北京盈科瑞创新药物研究有限公司 | 一种环己烷衍生物、制备方法及其应用 |
| TW202118758A (zh) * | 2019-11-05 | 2021-05-16 | 大陸商上海翰森生物醫藥科技有限公司 | 苯并噻吩類衍生物調節劑、其製備方法和應用 |
| 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 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666911A (en) | 1981-07-14 | 1987-05-19 | Taiho Pharmaceutical Company Limited | Allophanoylpiperazine compound and analgesic composition containing same as active ingredient |
| US4880797A (en) | 1986-03-20 | 1989-11-14 | Banyu Pharmaceutical Co., Ltd. | Cephalosporin derivatives and antibacterial agents |
| JPH01199977A (ja) | 1987-11-16 | 1989-08-11 | Mochida Pharmaceut Co Ltd | セファロスポリン誘導体の結晶、その製造法およびそれらを有効成分とする医薬組成物 |
| GB8802622D0 (en) | 1988-02-05 | 1988-03-02 | Glaxo Group Ltd | Chemical compound |
| 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 |
| JPH04275280A (ja) | 1991-03-04 | 1992-09-30 | Nippon Chem Ind Co Ltd | ４ｈ−２，３−ジヒドロ−２−イミノ−１，３−ベンゾチアジン−４−オン類の製造方法 |
| JPH0532586A (ja) | 1991-07-26 | 1993-02-09 | Mitsubishi Petrochem Co Ltd | ２，６−ナフタレンジカルボン酸の製造方法 |
| JPH05310745A (ja) | 1992-05-13 | 1993-11-22 | Takeda Chem Ind Ltd | ジエラジラクトンおよび抗炎症剤 |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| JP3696884B2 (ja) | 1994-03-25 | 2005-09-21 | アイソテクニカ、インコーポレーテッド | ジュウテリウム化による薬物の効能の増強 |
| WO1997011070A1 (en) | 1995-09-22 | 1997-03-27 | Warner-Lambert Company | Substituted cyclohexylamines as central nervous system agents |
| RU2230740C2 (ru) | 1998-03-31 | 2004-06-20 | Акадиа Фармасьютикалз, Инк. | Производные азотсодержащих гетероциклических соединений и фармацевтическая композиция на их основе |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| SE9802208D0 (sv) | 1998-06-22 | 1998-06-22 | Astra Pharma Inc | Novel compounds |
| KR20010053010A (ko) | 1998-06-30 | 2001-06-25 | 이베 사치아키 | 엔-페닐-엔'-페닐프로필피페라진 유도체 및 그의제조방법 |
| US6489341B1 (en) | 1999-06-02 | 2002-12-03 | Sepracor Inc. | Methods for the treatment of neuroleptic and related disorders using sertindole derivatives |
| BR0207832A (pt) | 2001-02-27 | 2004-06-22 | Ortho Mcneil Pharm Inc | Compostos de carbamato para uso na prevenção ou tratamento de distúrbio bipolar |
| 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 |
| 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 | |
| HU230748B1 (hu) | 2007-05-11 | 2018-02-28 | Richter Gedeon Nyrt | Új piperazin só és előállítási eljárása |
| HUE033357T2 (en) | 2007-05-11 | 2017-11-28 | Richter Gedeon Nyrt | Crystalline form of carbamoylcyclohexane derivatives |
| HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| 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 |
| 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 |
| US20100256145A1 (en) | 2007-08-01 | 2010-10-07 | H. Lundbeck A/S | Use of kcnq potassium channel openers for reducing symptoms of or treating disorders or conditions wherein the dopaminergic system is disrupted |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| WO2009104739A1 (ja) | 2008-02-21 | 2009-08-27 | 田辺三菱製薬株式会社 | 経口投与用固形製剤 |
| UA104869C2 (uk) | 2008-07-16 | 2014-03-25 | Ріхтер Гедеон Нірт. | Фармацевтичні композиції, що містять ліганди рецептора дофаміну |
| 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 |
-
2007
- 2007-05-18 HU HU0700353A patent/HUP0700353A2/hu unknown
-
2008
- 2008-05-15 AP AP2009005011A patent/AP2009005011A0/xx unknown
- 2008-05-15 NZ NZ580646A patent/NZ580646A/en unknown
- 2008-05-15 WO PCT/HU2008/000046 patent/WO2008142461A1/en not_active Ceased
- 2008-05-15 EA EA200971069A patent/EA200971069A1/ru unknown
- 2008-05-15 CN CN200880016466A patent/CN101679330A/zh active Pending
- 2008-05-15 JP JP2010508911A patent/JP5406827B2/ja active Active
- 2008-05-15 CA CA2684149A patent/CA2684149C/en not_active Expired - Fee Related
- 2008-05-15 BR BRPI0811744-6A2A patent/BRPI0811744A2/pt not_active IP Right Cessation
- 2008-05-15 MX MX2009012371A patent/MX2009012371A/es not_active Application Discontinuation
- 2008-05-15 EP EP08750836A patent/EP2155707B1/en active Active
- 2008-05-15 US US12/600,826 patent/US8765765B2/en active Active
- 2008-05-15 AU AU2008252619A patent/AU2008252619A1/en not_active Abandoned
- 2008-05-15 MY MYPI20094707 patent/MY150784A/en unknown
- 2008-05-15 GE GEAP200811607A patent/GEP20125523B/en unknown
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- 2009-12-16 CO CO09144002A patent/CO6251252A2/es not_active Application Discontinuation
- 2009-12-18 EC EC2009009819A patent/ECSP099819A/es unknown
Also Published As
| Publication number | Publication date |
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| NZ580646A (en) | 2012-03-30 |
| JP5406827B2 (ja) | 2014-02-05 |
| EA200971069A1 (ru) | 2010-04-30 |
| EP2155707B1 (en) | 2013-03-13 |
| HU0700353D0 (en) | 2007-07-30 |
| GEP20125523B (en) | 2012-05-25 |
| BRPI0811744A2 (pt) | 2014-11-11 |
| CN101679330A (zh) | 2010-03-24 |
| TN2009000459A1 (en) | 2011-03-31 |
| JP2010527983A (ja) | 2010-08-19 |
| ECSP099819A (es) | 2010-03-31 |
| CU23852B1 (es) | 2012-10-15 |
| CA2684149C (en) | 2012-12-04 |
| MY150784A (en) | 2014-02-28 |
| MX2009012371A (es) | 2009-12-03 |
| MA31432B1 (fr) | 2010-06-01 |
| US8765765B2 (en) | 2014-07-01 |
| NI200900202A (es) | 2010-03-11 |
| CU20090196A7 (es) | 2011-07-11 |
| AP2009005011A0 (en) | 2009-10-31 |
| CO6251252A2 (es) | 2011-02-21 |
| WO2008142461A1 (en) | 2008-11-27 |
| EP2155707A1 (en) | 2010-02-24 |
| HUP0700353A2 (en) | 2008-12-29 |
| US20100137335A1 (en) | 2010-06-03 |
| ZA200907425B (en) | 2010-07-28 |
| AU2008252619A1 (en) | 2008-11-27 |
| CA2684149A1 (en) | 2008-11-27 |
| IL201534A0 (en) | 2010-05-31 |
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