JP2005504126A5 - - Google Patents
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- Publication number
- JP2005504126A5 JP2005504126A5 JP2003532483A JP2003532483A JP2005504126A5 JP 2005504126 A5 JP2005504126 A5 JP 2005504126A5 JP 2003532483 A JP2003532483 A JP 2003532483A JP 2003532483 A JP2003532483 A JP 2003532483A JP 2005504126 A5 JP2005504126 A5 JP 2005504126A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- diastereomers
- stereoisomers
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 9
- -1 cyano, hydroxy Chemical group 0.000 claims 8
- 150000004677 hydrates Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 102000015554 Dopamine receptor Human genes 0.000 claims 4
- 108050004812 Dopamine receptor Proteins 0.000 claims 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229960003638 dopamine Drugs 0.000 claims 2
- 230000026030 halogenation Effects 0.000 claims 2
- 238000005658 halogenation reaction Methods 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 239000007790 solid phase Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KCJVTGHUUAEZOS-UHFFFAOYSA-N n,n-dimethyl-2-phenylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1 KCJVTGHUUAEZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008196 pharmacological composition Substances 0.000 claims 1
- 229920005990 polystyrene resin Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0103988A HU227543B1 (en) | 2001-09-28 | 2001-09-28 | 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 |
| PCT/HU2002/000093 WO2003029233A1 (en) | 2001-09-28 | 2002-09-25 | New sulfonamide derivatives as d3-receptor agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005504126A JP2005504126A (ja) | 2005-02-10 |
| JP2005504126A5 true JP2005504126A5 (enExample) | 2005-10-27 |
| JP4250082B2 JP4250082B2 (ja) | 2009-04-08 |
Family
ID=89979732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003532483A Expired - Fee Related JP4250082B2 (ja) | 2001-09-28 | 2002-09-25 | Ｄ３−受容体アゴニストとしての新規なスルホンアミド誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7473692B2 (enExample) |
| EP (1) | EP1438302B1 (enExample) |
| JP (1) | JP4250082B2 (enExample) |
| HU (1) | HU227543B1 (enExample) |
| PL (1) | PL210131B1 (enExample) |
| WO (1) | WO2003029233A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| SE521512C2 (sv) * | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| US20040048779A1 (en) * | 2002-05-06 | 2004-03-11 | Erwin Schollmayer | Use of rotigotine for treating the restless leg syndrome |
| DE60204229T2 (de) * | 2002-12-02 | 2006-02-02 | Schwarz Pharma Ag | Verabreichung von Rotigotine zur Behandlung der Parkinson'schen Krankheit durch Iontophorese |
| DK1803443T3 (en) * | 2002-12-20 | 2019-02-25 | Niconovum Ab | Nicotine-containing particulate material with a crystalline cellulose |
| DE10334187A1 (de) * | 2003-07-26 | 2005-03-03 | Schwarz Pharma Ag | Substituierte 2-Aminotetraline zur Behandlung von Depressionen |
| DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| HU227534B1 (en) * | 2003-08-04 | 2011-08-29 | Richter Gedeon Nyrt | (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them |
| US7196100B2 (en) | 2003-12-12 | 2007-03-27 | Eli Lilly And Company | Opioid receptor antagonists |
| DE10359528A1 (de) | 2003-12-18 | 2005-07-28 | Schwarz Pharma Ag | (S)-2-N-Propylamino-5-hydroxytetralin als D3-agonistisches Therapeutikum |
| EP1547592A1 (en) * | 2003-12-23 | 2005-06-29 | Schwarz Pharma Ag | Intranasal formulation of rotigotine |
| DE10361258A1 (de) | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
| EP1701970A2 (en) * | 2003-12-31 | 2006-09-20 | F.Hoffmann-La Roche Ag | Methods for recovering cleaved peptide from a support |
| DE102004014841B4 (de) | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
| HUP0500170A3 (en) | 2005-02-03 | 2007-11-28 | Richter Gedeon Nyrt | Piperazine derivatives, process for producing them and pharmaceutical compositions containing them |
| CA2646942C (en) | 2006-03-16 | 2014-07-29 | Modoral Brands Inc. | Improved snuff composition |
| EP1870405A1 (en) * | 2006-06-22 | 2007-12-26 | Bioprojet | Carbonylated (Aza)cyclohexanes as dopamine D3 receptor ligands |
| ES2401663T3 (es) * | 2006-10-31 | 2013-04-23 | F. Hoffmann-La Roche Ag | Derivados éter moduladores duales de los receptores de 5-HT2a y D3 |
| EP1987815A1 (en) * | 2007-05-04 | 2008-11-05 | Schwarz Pharma Ag | Oronasopharyngeally deliverable pharmaceutical compositions of dopamine agonists for the prevention and/or treatment of restless limb disorders |
| 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 |
| 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 |
| CN101778820B (zh) * | 2007-08-09 | 2012-12-05 | 弗·哈夫曼-拉罗切有限公司 | 作为5-ht2a和d3受体双重调节剂的苯甲酰基-哌啶衍生物 |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| KR20130115393A (ko) * | 2008-02-21 | 2013-10-21 | 미쓰비시 타나베 파마 코퍼레이션 | 경구 투여용 고형 제제 |
| AP2975A (en) | 2008-07-16 | 2014-09-30 | Richter Gedeon Nyrt | Pharmaceutical formulations containing dopamine receptor ligands |
| GB0817207D0 (en) * | 2008-09-19 | 2008-10-29 | Pimco 2664 Ltd | therapeutic apsac compounds and their use |
| WO2010031735A1 (en) * | 2008-09-22 | 2010-03-25 | F. Hoffmann-La Roche Ag | Piperazine d3 and 5-ht2a receptor modulators |
| 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 |
| US8912197B2 (en) | 2012-08-20 | 2014-12-16 | Forest Laboratories Holdings Ltd. | Crystalline form of carbamoyl-cyclohexane derivatives |
| WO2014086098A1 (zh) * | 2012-12-03 | 2014-06-12 | 江苏恒谊药业有限公司 | 环己烷胺类化合物及其作为抗精神分裂症药物的应用 |
| CN104140421B (zh) * | 2013-05-08 | 2017-04-05 | 上海医药工业研究院 | 苯并异噻唑类化合物及在制备抗精神分裂症药物中的应用 |
| ITMI20131693A1 (it) | 2013-10-14 | 2015-04-15 | Chemo Res S L | Derivati della 1,4-cicloesilammina e loro preparazione |
| GB201417168D0 (en) * | 2014-09-29 | 2014-11-12 | Univ Hertfordshire Higher Education Corp | Compounds |
| 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 |
| WO2018021447A1 (ja) | 2016-07-28 | 2018-02-01 | 塩野義製薬株式会社 | ドーパミンｄ３受容体拮抗作用を有する含窒素縮環化合物 |
| BR112020014875A2 (pt) | 2018-01-26 | 2020-12-08 | Shionogi & Co., Ltd. | Composto cíclico condensado tendo antagonismo de receptor de dopamina d3 |
| WO2019146740A1 (ja) | 2018-01-26 | 2019-08-01 | 塩野義製薬株式会社 | ドーパミンｄ３受容体拮抗作用を有する環式化合物 |
| US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047406A (en) * | 1989-12-06 | 1991-09-10 | Warner-Lambert Co. | Substituted cyclohexanols as central nervous system agents |
| SE9201138D0 (sv) * | 1992-04-09 | 1992-04-09 | Astra Ab | Novel phthalimidoalkylpiperazines |
| FR2742149B1 (fr) * | 1995-12-11 | 1998-02-13 | Inst Nat Sante Rech Med | Nouveaux derives de 2-naphtamides et leurs applications therapeutiques |
| RU2185372C2 (ru) * | 1996-05-31 | 2002-07-20 | Фармация Энд Апджон Компани | Алкилзамещенные циклические амины в качестве селективных лигандов d3-допамина |
| GB9708805D0 (en) * | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| PL336628A1 (en) | 1997-05-03 | 2000-07-03 | Smithkline Beecham Plc | Derivatives of tetrahydroisoquinoline as modulators of d3 dopamine receptors |
| DE19728996A1 (de) * | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
| GB9810876D0 (en) * | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| SK4782001A3 (en) * | 1998-10-08 | 2001-11-06 | Smithkline Beecham Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
| GB9821978D0 (en) * | 1998-10-08 | 1998-12-02 | Smithkline Beecham Plc | Compounds |
| TWI274750B (en) * | 1999-01-12 | 2007-03-01 | Abbott Gmbh & Co Kg | Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same |
| KR100394086B1 (ko) * | 2000-12-04 | 2003-08-06 | 한국과학기술연구원 | 도파민 ｄ3 및 ｄ4 수용체의 선택적 활성을 지닌 신규이소옥사졸릴알킬피페라진 유도체와, 이의 제조방법 |
-
2001
- 2001-09-28 HU HU0103988A patent/HU227543B1/hu unknown
-
2002
- 2002-09-25 JP JP2003532483A patent/JP4250082B2/ja not_active Expired - Fee Related
- 2002-09-25 PL PL370408A patent/PL210131B1/pl unknown
- 2002-09-25 WO PCT/HU2002/000093 patent/WO2003029233A1/en not_active Ceased
- 2002-09-25 US US10/491,150 patent/US7473692B2/en not_active Expired - Fee Related
- 2002-09-25 EP EP02765129A patent/EP1438302B1/en not_active Expired - Lifetime
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