AU2008252619A1 - Metabolites of (thio)carbamoyl-cyclohexane derivatives - Google Patents
Metabolites of (thio)carbamoyl-cyclohexane derivatives Download PDFInfo
- Publication number
- AU2008252619A1 AU2008252619A1 AU2008252619A AU2008252619A AU2008252619A1 AU 2008252619 A1 AU2008252619 A1 AU 2008252619A1 AU 2008252619 A AU2008252619 A AU 2008252619A AU 2008252619 A AU2008252619 A AU 2008252619A AU 2008252619 A1 AU2008252619 A1 AU 2008252619A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- optionally substituted
- alkoxycarbonyl
- compound
- aryl
- 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.)
- Abandoned
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- 239000002207 metabolite Substances 0.000 title claims description 20
- JMMKXVYQBRGGJF-UHFFFAOYSA-N cyclohexanecarbothioamide Chemical class NC(=S)C1CCCCC1 JMMKXVYQBRGGJF-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 108050004812 Dopamine receptor Proteins 0.000 claims description 15
- 102000015554 Dopamine receptor Human genes 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- -1 cyano, cyclohexyl Chemical group 0.000 claims description 13
- 150000004677 hydrates Chemical class 0.000 claims description 13
- 125000003435 aroyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 102000004980 Dopamine D2 Receptors Human genes 0.000 claims description 6
- 108090001111 Dopamine D2 Receptors Proteins 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 5
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 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 description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003235 pyrrolidines Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 102000005962 receptors Human genes 0.000 description 21
- 108020003175 receptors Proteins 0.000 description 21
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- 230000008485 antagonism Effects 0.000 description 7
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- 239000002585 base Substances 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- SFUUKZKRDDJCID-BCHJJPDRSA-N Cl.Cl.ClC1=C(Cl)C(OC)=CC=C1N1CCN(CC[C@@H]2CC[C@@H](N)CC2)CC1 Chemical compound Cl.Cl.ClC1=C(Cl)C(OC)=CC=C1N1CCN(CC[C@@H]2CC[C@@H](N)CC2)CC1 SFUUKZKRDDJCID-BCHJJPDRSA-N 0.000 description 3
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 206010026749 Mania Diseases 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000009871 nonspecific binding Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
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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
-
- 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
-
- 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
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- 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
-
- 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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| HUP0700353 | 2007-05-18 | ||
| PCT/HU2008/000046 WO2008142461A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008252619A1 true AU2008252619A1 (en) | 2008-11-27 |
Family
ID=89987527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008252619A Abandoned AU2008252619A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8765765B2 (https=) |
| EP (1) | EP2155707B1 (https=) |
| JP (1) | JP5406827B2 (https=) |
| CN (1) | CN101679330A (https=) |
| AP (1) | AP2009005011A0 (https=) |
| AU (1) | AU2008252619A1 (https=) |
| BR (1) | BRPI0811744A2 (https=) |
| CA (1) | CA2684149C (https=) |
| CO (1) | CO6251252A2 (https=) |
| CU (1) | CU23852B1 (https=) |
| EA (1) | EA200971069A1 (https=) |
| EC (1) | ECSP099819A (https=) |
| GE (1) | GEP20125523B (https=) |
| HU (1) | HUP0700353A2 (https=) |
| IL (1) | IL201534A0 (https=) |
| MA (1) | MA31432B1 (https=) |
| MX (1) | MX2009012371A (https=) |
| MY (1) | MY150784A (https=) |
| NI (1) | NI200900202A (https=) |
| NZ (1) | NZ580646A (https=) |
| TN (1) | TN2009000459A1 (https=) |
| TW (1) | TW201002324A (https=) |
| WO (1) | WO2008142461A1 (https=) |
| ZA (1) | ZA200907425B (https=) |
Families Citing this family (19)
| 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 |
| KR101563383B1 (ko) * | 2008-02-21 | 2015-10-26 | 미쓰비시 타나베 파마 코퍼레이션 | 경구 투여용 고형 제제 |
| PL2317852T3 (pl) | 2008-07-16 | 2015-05-29 | Richter Gedeon Nyrt | Preparaty farmaceutyczne zawierające ligandy receptora dopaminy |
| 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 |
| BR112012010670A2 (pt) * | 2009-11-06 | 2016-04-12 | Sk Biopharmaceuticals Co Ltd | métodos para tratamento de distúrbio de défict de atenção/hiperatividade |
| US20110117214A1 (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 |
| US8912197B2 (en) | 2012-08-20 | 2014-12-16 | Forest Laboratories Holdings Ltd. | Crystalline form of carbamoyl-cyclohexane derivatives |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
| US12319659B2 (en) | 2017-02-24 | 2025-06-03 | Shenzhen Linglan Bio-Pharmaceutical Technology Co., Ltd | Selective ligand for dopamine D3 receptor, preparation method therefor, and pharmaceutical application thereof |
| 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 |
| US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
| HU231500B1 (hu) | 2019-04-10 | 2024-04-28 | Richter Gedeon Nyrt | Karbamoil-ciklohexán származékok autizmus spektrum betegség kezelésére |
| 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 |
| JP7810643B2 (ja) * | 2019-11-05 | 2026-02-03 | 上▲海▼翰森生物医▲薬▼科技有限公司 | ベンゾチオフェン誘導体レギュレーター、その調製法及び使用 |
| EP4594294A1 (en) * | 2022-09-30 | 2025-08-06 | 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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| US6528529B1 (en) * | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
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| SE9802208D0 (sv) | 1998-06-22 | 1998-06-22 | Astra Pharma Inc | Novel compounds |
| US6395739B1 (en) * | 1998-06-30 | 2002-05-28 | Zeria Pharmaceutical Co., Ltd. | N-phenyl-N′-phenylpopylpiperazine derivatives and process for the preparation |
| US6489341B1 (en) * | 1999-06-02 | 2002-12-03 | Sepracor Inc. | Methods for the treatment of neuroleptic and related disorders using sertindole derivatives |
| US7122576B2 (en) * | 2001-02-27 | 2006-10-17 | Plata-Salaman Carlos R | 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 |
| 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 | |
| ES2617671T3 (es) * | 2007-05-11 | 2017-06-19 | Richter Gedeon Nyrt. | Forma cristalina de un derivado de carbamoil ciclohexano |
| HU230748B1 (hu) | 2007-05-11 | 2018-02-28 | Richter Gedeon Nyrt | Új piperazin só és előállítási eljárása |
| 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 |
| CN101790374A (zh) * | 2007-08-01 | 2010-07-28 | H.隆德贝克有限公司 | Kcnq钾通道开放剂用于减轻多巴胺能系统受到干扰的障碍或病症的症状或治疗这种障碍或病症的用途 |
| US7875610B2 (en) * | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| KR101563383B1 (ko) * | 2008-02-21 | 2015-10-26 | 미쓰비시 타나베 파마 코퍼레이션 | 경구 투여용 고형 제제 |
| PL2317852T3 (pl) | 2008-07-16 | 2015-05-29 | Richter Gedeon Nyrt | Preparaty farmaceutyczne zawierające ligandy receptora dopaminy |
| 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 |
-
2007
- 2007-05-18 HU HU0700353A patent/HUP0700353A2/hu unknown
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2008
- 2008-05-15 AP AP2009005011A patent/AP2009005011A0/xx unknown
- 2008-05-15 CN CN200880016466A patent/CN101679330A/zh active Pending
- 2008-05-15 MY MYPI20094707 patent/MY150784A/en unknown
- 2008-05-15 EA EA200971069A patent/EA200971069A1/ru unknown
- 2008-05-15 CA CA2684149A patent/CA2684149C/en not_active Expired - Fee Related
- 2008-05-15 WO PCT/HU2008/000046 patent/WO2008142461A1/en not_active Ceased
- 2008-05-15 NZ NZ580646A patent/NZ580646A/en unknown
- 2008-05-15 AU AU2008252619A patent/AU2008252619A1/en not_active Abandoned
- 2008-05-15 JP JP2010508911A patent/JP5406827B2/ja active Active
- 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 GE GEAP200811607A patent/GEP20125523B/en unknown
- 2008-05-15 EP EP08750836A patent/EP2155707B1/en active Active
- 2008-05-15 US US12/600,826 patent/US8765765B2/en active Active
- 2008-07-08 TW TW097125708A patent/TW201002324A/zh unknown
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2009
- 2009-10-15 IL IL201534A patent/IL201534A0/en unknown
- 2009-10-22 ZA ZA200907425A patent/ZA200907425B/xx unknown
- 2009-10-30 TN TNP2009000459A patent/TN2009000459A1/fr unknown
- 2009-11-09 NI NI200900202A patent/NI200900202A/es unknown
- 2009-11-17 CU CU2009000196A patent/CU23852B1/es not_active IP Right Cessation
- 2009-12-07 MA MA32403A patent/MA31432B1/fr unknown
- 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 |
|---|---|
| GEP20125523B (en) | 2012-05-25 |
| JP2010527983A (ja) | 2010-08-19 |
| CU20090196A7 (es) | 2011-07-11 |
| MY150784A (en) | 2014-02-28 |
| IL201534A0 (en) | 2010-05-31 |
| MA31432B1 (fr) | 2010-06-01 |
| ECSP099819A (es) | 2010-03-31 |
| TN2009000459A1 (en) | 2011-03-31 |
| US20100137335A1 (en) | 2010-06-03 |
| EP2155707B1 (en) | 2013-03-13 |
| BRPI0811744A2 (pt) | 2014-11-11 |
| ZA200907425B (en) | 2010-07-28 |
| CN101679330A (zh) | 2010-03-24 |
| AP2009005011A0 (en) | 2009-10-31 |
| EP2155707A1 (en) | 2010-02-24 |
| CA2684149A1 (en) | 2008-11-27 |
| NZ580646A (en) | 2012-03-30 |
| JP5406827B2 (ja) | 2014-02-05 |
| NI200900202A (es) | 2010-03-11 |
| WO2008142461A1 (en) | 2008-11-27 |
| EA200971069A1 (ru) | 2010-04-30 |
| HU0700353D0 (en) | 2007-07-30 |
| HUP0700353A2 (en) | 2008-12-29 |
| CU23852B1 (es) | 2012-10-15 |
| CO6251252A2 (es) | 2011-02-21 |
| TW201002324A (en) | 2010-01-16 |
| MX2009012371A (es) | 2009-12-03 |
| US8765765B2 (en) | 2014-07-01 |
| CA2684149C (en) | 2012-12-04 |
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